4-time Emmy Award-winning Screenwriter & Executive Producer of The Sopranos, Creator of HBO’s Boardwalk Empire and Oscar-nominated Writer of The Wolf of Wall Street – Terence Winter, is on REINVENTED! Terence and Jen discuss how he went from being a New York City taxi cab driver, hospital security guard, doorman, and paperboy to reinventing himself as a Hollywood screenwriting legend. He shares why he decided to quit his comfortable job as a lawyer, move to LA and never look back. Terence also shares advice to anyone wanting to quit their 9-5 PM job to pursue something greater in life. He also shares funny stories working with Leonardo DiCaprio, Matthew McConaughey, Martin Scorsese, Mick Jagger, James Gandolfini, 50 Cent, and Sylvester Stallone. Terence also talks about meeting Jordan Belfort, his ex-wives, and the FBI agent who arrested him while making The Wolf of Wall Street, which was nominated for 5 Academy Awards. Terence and Jen even get into actor Will Smith physically assaulting comedian Chris Rock at the Oscars!

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REINVENTED With Oscar-nominated Hollywood Screenwriter Terence Winter

JE: You've heard me say on this show before that my true heroes in life are people who have known defeat, people who have known what it means to struggle and have had to fight, scratch and claw their way to get to where they are now. No handouts, no rich parents, no trust funds, no favors, just straight-up hustle every single day.

It takes a very special person to overcome adversity and make it to the top. My next guest's incredible journey of reinvention, sheer willpower and determination are what this show is all about. In this episode, Reinvented is going Hollywood. That's right. We have Terence Winter in the house. He is the Creator and Executive Producer of HBO's Award-Winning drama series, Boardwalk Empire. He also co-created and was the Executive Producer of the rock and roll drama series Vinyl.

Terry was also one of the Writers and Executive Producers of The Sopranos, for which he was honored with 4 Emmy Awards as well as 3 Writer's Guild Awards. In 2014, he was also nominated for an Academy Award for his screenplay writing The Wolf of Wall Street. Terry, I'm out of breath listing your resume. It's extremely intimidating, and I haven't even begun to scratch the surface of the high-profile people you've worked with. We got Leo DiCaprio, Matthew McConaughey, Martin Scorsese, Mick Jagger, James Gandolfini, and even 50 Cent. The list goes on and on. Do you ever stop and pinch yourself like, “Is this really my life?”

TW: I'm doing it now. Hearing that introduction, I'm like, “Who is she talking about? That's me. I did all that stuff.” Honestly, there are times when I have to stop and take a moment and take it in and smell the roses, basically. I remind myself, “This is what you worked for. This is what is supposed to have happened. This was the plan.”

People are very fond to talk about luck, and I always say to people, “It's funny. The harder I work, the luckier I seem to get.” A lot of it has to do with that. This was, again, a very long-standing plan from a childhood of like, “How do I get from here to there?” Thank God, it worked. A lot of people work hard and don't have the success I have been blessed to have, and it's not a given if you would work hard.

JE: It wasn't handed to you.

TW: Not even remotely.

JE: That's why I wanted to bring you on my show because you are emblematic of what it means to reinvent oneself. You've done it all. You name a job. You’ve done it. At one point, you were a taxi cab driver. You were a hospital security guard, a New York Times paperboy even. You were responsible for neighborhoods in Brooklyn at 21 years old.

TW: I was a paper boy as an adult, which isn’t even worse. I couldn't get a paper out when I was a kid. I didn't deliver newspapers until I was in my twenties when I was in law school and college.

JE: You were able to legally drink and party around town, and here you are, delivering 400 Sunday Times at 3:00 the morning.

TW: Those are some rough years, but those are all character builders. Very early on, I said I had to figure out how to get from where I was to where I wanted to go. I grew up in a blue-collar neighborhood in Brooklyn. It was a perfectly nice place. I was the last of five kids. My dad sadly passed away when I was young, and my mom was a secretary. We did okay but I had this idea that there was something more. I would see people with money who were successful. I was like, “How do I do that?” Unfortunately, based on where I come from and what you are exposed to, I didn't have a lot of role models.

I didn't know anybody. I was the first person in my family who went to college. Later on, some of my older siblings did as well at high school but I didn't know a lawyer or a doctor. It depends on where you are from. It's interesting that now I’m in Hollywood. Your next-door neighbor is an editor or this guy is an actor. It's like living in Pittsburgh at the height of the steel industry. Everybody is in that industry.

In Brooklyn in the ‘70s, nobody. The idea of going to Hollywood was not even a dream at that point for me. At that point, the dream was, “How do I become successful? How do I become rich?” I was always a very hard worker but didn't know how to get from A to B. Very early on. I got my first job when I was ten, delivering borders for a local pharmacy, then I worked at a butcher shop delivering meat there.

JE: You even worked the graveyard shift. Can you tell I'm a journalist? I have done my research on you. Midnight to 8:00 AM as a doorman at an apartment building on the Upper Eastside.

TI: Yes, then I went to school during the day. The interesting thing about the job was delivering meat for the butcher shop, in addition to the fact that it was owned by Paul Castellano, who was the head of the Gambino Family. That gave me a little research for later on.

JE: That information came in handy later in life.

TW: In terms of life development, what it did for me is it allowed me to go into other people's homes. It showed me how other people lived. I would go into houses that were much nicer than mine. Again, five kids. My mom was a secretary. My house was a crazy chaotic mess but I would go into these houses where everything is clean and neat. The dad wore a college shirt, and they had art on the walls and books.

I was slowly saying, “I want that.” It's funny. There was one house in my neighborhood. The house in Marine Park, Brooklyn, the houses are very tiny, maybe 1,100 square feet. I'm talking about a three-bedroom house. There was one house a couple of blocks away that was 2,000 square feet. When I delivered meat for the butcher shop, I used to go out of my way to drive down that street to look at that house and go, “One day, I'm going to have a house like this.”

It's funny now because it's still a tiny house but then, again, I was a kid who delivered meat for a butcher shop. I went to high school to study to be an auto mechanic. Talk about reinventing myself. I had no idea what I was doing or where to go and how to get, again from A to B. All I knew is I wanted to be successful. We had a mall in my neighborhood, the Kings Plaza Shopping Mall, where I used to go there for motivation. I used to walk around the mall and go into Macy's and the furniture department. I was like at 13 and 14 and walk through the Macy's Furniture Department and go, “One day, I'm going to have all this fancy stuff.”

JE: That's like the equivalent of Pinterest.

TW: It was a live action version of Pinterest. I would see all this like fancy stuff, “One day, I'm going to have that big Chinese bedroom set.” This big oriental phase back then. That was the style they called it. I saw all this cool stuff, and that used to get me pumped up. It’s like, “I want to be successful.” Again, I had no real role models. I didn't know anything about Wall Street, business or anything. The only two jobs I knew that were successful were doctor and lawyer, and the doctor was out.

This was years later when I set my eyes on law school. Even getting there was a very securest route. I had worked during high school, did the butcher shop job and then on the weekends, I waxed cars and also worked at a synagogue as a waiter. Even though I went to a Catholic school. I was the waiter at weddings and bar mitzvahs in the local city. I hustled like crazy. I used to always say to people, “You may be smarter than me but you will never outwork me. I will work you to death.”

JE: You appreciate the finer things in life because of your humble beginnings. I am curious, what would cab driver/doorman Terry Winter say to Terry Winter now?

TW: It was because you were a cab driver and a doorman that you are Terry Winter now. Also, Terry Winter now knows how to treat cab drivers and doormen very well because I was them. I was there. It's interesting. I always take note of how people treat waiters or if somebody is a crappy tipper, this person has never worked for tips. If you ever worked for tips, you would be an over-tipper because you have been there.

JE: I've always believed in treating the janitor the same way as the CEO. That's how I was raised.

TW: Great example. I had a car. I came back from Oklahoma City, and a woman picked me up at 11:00 at night with a limo driver, and we started chatting. She is working on her post-Doctorate in Neuroscience. This is the limo driver and a brilliant woman. We had this fascinating conversation about the brain's ability to repair itself after trauma. This is a woman driving a limo. She said, “This is the only way I could do this. I literally have to do 5,000 hours of work to finish my post-Doctorate work, and this is how I support myself.” I said, “Good for you.”

It's interesting how we did not have that conversation. It's very easy for somebody to go, “Look at this woman driving a limo or whatever.” This is one of the smartest people I have ever met, and I met a bunch of them like that. You can never underestimate or assume anything about people because that hustle that drive is what got her into that Doctoral program.

You can never underestimate or assume anything about people.

JE: Give her my contact information because, honestly, I would love to have her on. That's what this show is all about. One thing that did stand out to me on your bio, and no offense to any lawyers out there but it's not often that you see the word standup comic and former lawyer in the same biography. I'm not sure I've ever met a funny attorney in my life. No offense to my father, who is the best attorney I know who's probably reading this episode.

You paid for both college at NYU and law school at St John's University with student loans. You are, as you said, the first person in your family to go to college. After graduating from law school, you are on this partnership track at a major Manhattan law firm. What was the internal monologue you had with yourself that was like, “Screw this. I'm going to quit. I'm going to move to LA where I have never been before, and I'm going to start writing scripts?” How does that happen?

TW: The internal monologue was more of an internal groaning and thinking, “I made a horrible mistake.” My whole life again was geared toward, “I'm going to be successful. I want to make money.” Again, it was a doctor or lawyer. I come out of auto mechanic school, so a real circuitous route through NYU and working at night and driving to chem and all that stuff. Finally, get to law school, and I didn't like it but thought, “Nobody likes their job,” but at least you will make a lot of money.

JE: You just accepted the misery.

TW: I did not like my job as a lawyer than not like my job as a janitor so that I will make more money. I didn't realize how much I wouldn't like it. I was in a big corporate law firm and it was, to me, the driest soul-sucking work I can imagine. It was all filling out forms for SEC filings and stuff. Very early on, within a week, I realized I had made a grave error.

I spent the next two years living this life of quiet desperation and thinking, “What am I going to do? I can't possibly continue this.” Also, I was horrible at it because I didn't care. I was sneaking out of work during the day to go to the movies. I was going to bookstores. The only thing that saved me in that job was that I was a good writer.

I used to write good memos and research and all that stuff. Slowly, it got to the point where I didn't want to get up and go to work in the morning. I was approaching 30, which is a very key time in a person's life. You start to evaluate where you are going, and you got a long road ahead of you. I finally slowly started dipping my toe in the water, “What if I did something else?”

The internal monologue, as you said, was that maybe I could be in sales because I like to talk. I like people and there was a little voice in my head that says, “It's not sales. What is it?” I said, “Maybe advertise. Maybe a copywriter,” and it's like, “It's not that. Go deeper.” The deep dark secret was that I wanted to be a writer. I wanted to be a specifically a sitcom writer. It was always funny, and my friends and family thought it was funny.

It's interesting. In the movie Mr. Saturday Night with Billy Crystal, he plays a standup comic in the ‘50s. He talks about the difference between, he calls it living room balls or real balls. Living room balls are standing up in front of your friends and family and being funny. Real balls are getting up on a stage and trying to do it for an audience.

I said, “I wonder if I only have living room balls. I got to see.” More importantly, I say, “I got to see if I'm funny. I think I'm funny but if I'm going to be a comedy writer, I'm going to give up law and go to LA and do this.” The fastest way to see is to write your own material and go and perform it, so I did. For a couple of months in the early ‘90s, I performed a characterizing star and the comic strip in a couple of places in Manhattan.

I always got on at 2:00 in the morning, and it worked. It was okay. I did fine. I got people laughing. I was like, “You are not crazy. You can do this,” then it was talk about reinventing. I had to look at my family and friends and say, “I'm going. This is what my plan is.” My friends are my folks from Brooklyn. They say, “You are the first person in your family to attend college. You go to NYU. You go to law school. You pass the New York Bar and the Connecticut Bar.”

JE: This is not an easy thing to do.

TW: Anybody who does that, my hat's off. That is not easy. “You are now going to quit your big job at a Manhattan law firm and move to California. You have never been West of Chicago and you are going to write scripts. You've never written a script before. What plan is this?” I was like, “I know that sounds crazy but I'm telling you, I'm right.”

They said, “You are going to be back here in six months.” I said, “I don't think so.” I got on a plane and did that. I have to say, it was the most exhilarating feeling because when I would wake up in Los Angeles and I would be in this strange place every day. I was like, “What am I doing here? I know what I'm here. I knew what I needed to do.” I was fired out of a cannon every morning.

I couldn't wait to get there because I knew what I wanted. Finally, for the first time in my life, I wanted this as opposed to law school, which was like a slog of, “I got to study.” This was, “I'm going to go.” I lived, eat, ate and breathed writing for two years straight. I got a job to pay my bills and lived like a monk. I was writing. I said, “I am going to make this happen,” and threw myself into it.

JE: It certainly has paid off for you. There's so much truth in that. You went to LA, never having been West of Chicago before. You threw yourself into the situation. I've always said that's where the magic happens when you take yourself out of your comfort zone.

TW: There's something incredible about taking yourself out of that zone because you start to rely on old habits. It's so easy to go, “I will do it tomorrow. I will write tomorrow.” It's funny. What ended up happening is that I was this pioneer. I showed up in LA, and suddenly, all my friends started coming out of the closet as actors and were like, “I always thought about going to Hollywood.”

JE: Funny how that happens.

TW: I'm single-handedly responsible for eighteen more people moving out here. Some of whom are still doing and did it and working. One of my best friends in the world was an actor named Chris Caldovino, who has been on Sopranos, Boardwalk Empire, and a bunch of different TV shows. He's done it. When a lot of those people came out, we would get settling, “We are going to go to the Dodger game.” I go, “I didn't come here to go to the Dodger game. I came here to make it as a writer.”

JE: “I didn't come here to watch baseball. I'm here to win an Oscar.”

TW: When that happens or when I'm working as a writer, I will go to the Dodger game. Until then, I am not doing anything else that distracts me from what I'm here to do. Again, I was almost 30. It wasn't 22. I felt like I took a detour and got to make this happen. There was a ticking clock for me and I was like, “I am going to make this happen now.” It's again very easy to get distracted and say, “I will do it tomorrow.”

Writing is like any other career where you have to be a self-starter, come home at the end of the day, have your day job, and sit down. It's 7:00 at night, and you turn on that computer screen and look at a blank screen computer. It’s like, “Go ahead, make it happen.” Unless you do it, the words don't appear magically. It's challenging. People who say, “I want to write a script.” You should do it. You should lock yourself in a room with a blank computer screen, sit there for six hours, and come out and tell me how much fun you had.

JE: Writer's block is a real thing. What advice do you have for aspiring writers out there who want to sit down and leave their 9:00 to 5:00 gig to pursue something greater like what you did? How do you get out of that negative mindset? How do you cure writer's block?

TW: It is a craft like any other craft. It is very different but it's similar, I will say to build a bookcase, for example. A story has a structure. It has a beginning, a middle and an end. A bookcase has a frame, a back, got two sides, a top and a bottom. There are very rudimentary skills you can rely on to start the work. Even if I'm writing a script, I know a little bit of what it's about. If I have a scene, you and I meet for lunch to talk about getting divorced.

I know what the scene is about, so we sit down. Even if I'm blocked and don't have any interesting creative way into it, I know basically what this is. I will write the worst version of that scene. Interior restaurant, Terry and Jen sit down over coffee. Terry says, “This is obviously a very difficult conversation to have,” but I just write whatever is the most basic. At least a couple of minutes later or an hour later, I've got a couple of pages with ink on them.

JE: It’s a start.

TW: It's something. Force yourself to get something in there.

JE: Putting thoughts on paper.

TW: Rather than bang your head against the wall. The other thing I do is I don't force it. If I'm not feeling it, I will go and do something else because you are still thinking about it. I won't sit in front of this computer and whine and cry. I will say, “If it's not working, I will go take my dogs out” but I'm still thinking about what I'm doing, and then I will come back to it a little later. Don't do that a lot because that's also known as procrastination, which is probably not good.

It's a career that requires you to be a real self-starter. You've got to be able to sit down and do it. Sometimes even when you are working on a set or a show, at the end of the day, sometimes the casters go, “We are going to go out for drinks.” I feel like, “I have homework. I have to go home and work on a script,” and it sucks because I want to go out and get drunk and have fun but I'm like, “I have to go upstairs to my room and do this.”

JE: Terry, I speak for everyone in saying, “Thank you for leaving your boring law job to move to Hollywood.” We have the Sopranos now to thank for it. Look at this incredible creation of yours, Boardwalk Empire. I worked for a national news network for nearly a decade here in New York City after leaving the company in 2020.

After working in the corporate world for so long, you have to regain your footing in life. It has allowed me to unleash my creativity, hence launching this show. You were being held back, and I'm a little late to the party. Who am I kidding? I'm extremely late to the party. Don't kill me but I watch The Sopranos prior to this interview. I'm not even kidding.

TW: I don't think my wife has seen all the Sopranos. She has been lying to me all these years because occasionally, I will reference something, and she will go, “What?” I go, “It's from the Sopranos.” She goes, “Oh yes, right.” I’m completely fine. All is forgiven. I don't assume anybody's watched anything because I don't watch anything.

JE: I like doing my research. I'm like a method actor in that way. I have to get into the role. I have to live it, eat it and breathe it. I literally locked myself in my apartment for five days straight and binged all seven seasons. Do I get some awards for that?

TW: You must get some. I will teach you the secret handshake.

JE: Incredible show. Pine Barrens, I will say my favorite episode. I know that is a fan favorite. When I looked up who the writer was, it was you. Shocker. I have to know. I have a burning question. This was also a couple of friends of mine. I asked them, “Do you have any questions for Terry Winter?” They said, “Yes, what happened to the Russians in Pine Barrens?” What happened to him? Where did he go?

TW: We don't know. We don't. That's the great thing about doing a show like that. Part of the brilliance of David Chase is that he quoted somebody. I don't know who said this originally but he said, “Art asks questions. It doesn't give answers.” If you use that as a framework for your own work, you go, “Not every single thing has to be wrapped up in a bow.” We, as an audience, are so trained from decades or now a century of entertainment to extract that at the end.

They are going to tell you who the murderer is and what happened, and it's all wrapped up in a bow, and then you can leave. It's much more satisfying, sometimes, to go, “We don't know what happened.” It's to go, “What a mystery.” The fact that we are still having this conversation about what happened, I don't know. He's either escaped, got found by Boy Scouts who took him and rehabilitated him and went back to Russia. He's a ghost. It could be anything, which for me, is so much more interesting than, “We have the definitive answers.”

JE, I get it. I like it. It leaves it up to interpretation.

TW: It does bug people who have that need to foreclosure. There's something to be said for them. On the other hand, there's something to be said for, “I don't know.”

JE: It's funny. I was reading an interview. I'm fresh off the show and still processing the ending. I'm not going to lie. It was a little rude. Not the biggest fan. I did think there was something wrong with my TV after it went dark.

TW: You and everybody else.

JE: Only what, 10 or 15 years later? Anyway, I have to know, and I was reading an interview with David Chase. He basically echoed your sentiment about keeping the dialogue alive and keeping people guessing and wondering. I appreciate that factor but then he was like, “People wanted to see him shot face down.” I was like, “I did want to see that.” I have to know, what is your interpretation of the ending? How do you see it ending?

TW: David's intention was to subvert expectations, which is what we all try to do. It is very difficult in this business. The biggest compliment somebody can give me as a writer is to go, “I didn't see that coming. That was surprising.” Again, for so many years, we always know it's coming. For me, to pull the wool over your eyes as an audience is challenging.

For so many years, we always know it's coming. So to pull the wool over the eyes of the audience is challenging for a writer.

After 100 years of watching cinema and knowing the language of film, and knowing where things are going to go, it's always great. It started from that place of Dave saying, “I want to do something different.” My interpretation of it is whether or not Tony got killed that night or some other night. At some point, somebody is going to walk out of a men's room somewhere, and it's going to be over. Maybe it happened that night. Maybe it didn't but the idea, the takeaway is that when you are Tony Soprano, he always knows.

JE: You are always looking behind your back.

TW: Even going out for ice cream with your family is fraught with paranoia. You will never ever be able to completely relax. That was the takeaway. Again, maybe it happened that night. Maybe it didn't. It doesn't matter. At some point, either he's going to get killed or he's going to live a life of that anxiety.

JE: I was having anxiety watching Meadow try to parallel park her car for like ten minutes.

TW: It was all designed toward it. It was building toward that you think something is going to happen, then maybe it did. Again, the same with for the Russians. Who knows?

JE: Is that how you would've ended the series if it were up to you?

TW: I would've ended this series by having a very old Steve Buscemi as Nucky come into the restaurant and kill Tony Soprano. He would have been 105 years old, so that's a different show. I don't know. I have no idea how I would've ended it.

JE: People are so intrigued by James Gandolfini who portrayed Tony Soprano on the show. I would imagine that you and James were close. Everyone seemed to adore him. His passing was sudden and shell-shocked everyone who loved the Sopranos and him as an actor. If he were still alive now, where do you think James Gandolfini would be in his career?

TW: Anywhere he wanted. His trajectory as an actor would've continued. He was an incredible actor. Fearless in the sense that had no ego and the ability to divorce yourself from your own image and what you look and sound that feel like is so challenging. I won't even say I've acted before. I have been in things. I would never call myself an actor but it's hard not to be self-conscious.

The ability to divorce yourself from your own image and what you look, sound, and feel like is so challenging.

Jim had the ability to completely forget himself and be. The things he did after the Sopranos, if you see one of the last things he ever did, was a movie called Enough Said with Julia Louis-Dreyfus. It's interesting. More than anything, that guy he played in that movie was closest to the real person you've ever seen. Very kind, funny, gentle, giant, and self-deprecating. He was nothing like Tony Soprano in real life.

JE: That's a sign of a good actor when you are able to completely transform yourself and immerse yourself into that character.

TW: He was a gentleman, funny, kind, incredibly generous and an incredible actor. Unbelievable. I would stand in awe 5 feet away, watching him work. It's pretty incredible. Again, for people who don't do this, it's very easy for people to go, “Actors, what's my motivation?” When I hear people do that, I go, “You've never acted. You've never tried to do this. It's hard.” When you got people who do it well, it's years of work. Sometimes even after that, they don't have that thing. I'm not talking about being a movie star. I'm talking about being an actor. A movie star is what occasionally happens to actors if they get incredibly lucky. Being an actor is a whole different ball of wax. It's a tough thing to do.

JE: It's a craft like being a writer. I would be lying if I said that some of the episodes were not triggering for me as a woman to watch. We have an open and honest conversation. I'm not a fan of the way that they treat women on the show but I will say I'm of two minds about it because I do admire this series for tackling the difficult subject matter.

The Sopranos was truly the first of its kind out there to push the envelope and explore new boundaries in television. I've noticed that a lot of the subject matter that you write about tends to be dark in nature, mobsters, drug addiction, domestic violence, money laundering, and jail. Those are the central themes of the shows you write. What is it about that particular dark genre that entices you and draws you in as a writer?

TW: I'm crazy.

JE: Refreshingly honest answer.

TW: It’s so funny because, in real life, I'm the most boring guy in the world. I'm a homebody. I play with my dogs. I'm dull but in my career, fantasy, I have always been fascinated by people who live outside the boundaries of the law. A lot of us are. There's a genre of crime drama, and we are always looking like, “How do people do that? What makes somebody like that tick?” It's funny, somebody asks me, “How did you start writing about crime?” I trace it back to the movie Oliver, the Musical.

JE: I was going to say your Brooklyn roots, perhaps.

TW: That coupled with. I saw Oliver Twist and was like, “I wanted to be part of that gang of pickpockets.” It was so cool. The idea of using your wits to steal money, and then I was interested in conmen. I watched The Sting. In my neighborhood in Brooklyn, working in the butcher shop, and then read about the MOB and watched Warner Bros gangster movies. It all started to morph into this fascination.

I realized by osmosis that I understood how these guys behaved, how they talked, what their psychology was and all of that. It came naturally to me, and then I had an outlet for it when I got to Hollywood. During the first seven years of my career, I was writing Sister, Sister, a teen comedy. I wrote about the new adventures of Flipper, Xena Warrior Apprentice. There's nothing in my resume that would suggest what to write.

JE: I don't think I'd ever put the Sopranos and Flipper in the same sentence. I love that.

TW: There were ducks in there but no dolphins. When the Sopranos came along, my agent at the time, who knew my background, said, “You got to see this show.” I was like, “I know these folks. I know this world. You got to get me on the show.” I was lucky enough to have that happen, and that changed everything for me.

JE: You are also the Creator of HBO's Boardwalk Empire and what is special about that project is that it's entirely your creation. That is your baby. It's pretty clear that you have an interest in the history of the American Mafia. Are there any plans to revive that series somehow and bring it back to life?

TW: No, I think we ran a full circle. I should say that was based on a nonfiction book about Atlantic City. The series was my creation but it was based on a book in broad strokes by a guy named Nelson Johnson, who's a wonderful writer and a judge in New Jersey. We told the story. We took that character full circle. It was basically the story of the prohibition of Atlantic City during prohibition. I'm very comfortable leaving it.

JE: The people want more, Terry. Give the people what they want.

TW: They want more, and you think we squeeze a little more juice out of the orange? I'm more comfortable saying this is it. This is the show. There's no more. Hopefully, you like it and leave it where it is.

JE: I have to know, The Many Saints of Newark movie that came out, why were you not a part of that?

TW: I was busy. I was working on a bunch of other stuff. I was cheering David from the sidelines. I said, “If you do another one, I’m out.” I couldn't do it. I liked it. I thought he did a great job, he and Larry Connor. It’s endlessly fascinating to Sopranos in that world and that whole universe. It's almost what they are doing with Star Wars now, where they expanded into different stories.

That's what's great about doing long-form storytelling, TV series. You build a world. When I started with the pilot of Boardwalk Empire, again, the book was based on the history of Atlantic City. There was this one character named Nucky Johnson, who I fictionalized as Nucky Thompson. Started with that character, and then there was an encounter with this woman that he talked about in the book, a woman in the neighborhood who came and asked to help him get her husband a job. It started with that little idea and expanded into five seasons of backstories, history, and different interactions between characters. You are creating this fictional universe, and it's satisfying as a storyteller.

JE: I try to take myself into the writer's room. I don't know why but I picture you folks with a dart board and throwing or even throwing spaghetti at the wall and seeing what sticks like, “Which idea is going to work here? What's going to jive?”

TW: It all starts with what if. “What if this? What if that?” There's no bad idea because a bad idea might lead to a good idea. Usually, people go, “This isn't it but what if such and such happens?” They always qualify. “This is stupid but,” because you feel the need to give yourself some disclaimers. Some of the best ideas come out of jokes, kidding around or you don't know where they are going to come from. That is the dart board without the darts.

It all starts with what if – what if this or what if that? - but there's no bad idea, because a bad idea might lead to a good idea.

JE: You are not throwing spaghetti at the wall, seeing what sticks.

TW: I don't waste spaghetti.

JE: I have to know, what was it like to work with screenwriter legend Martin Scorsese on Boardwalk and again on the Wolf of Wall Street? I'm curious to know if there was ever a piece of advice he gave you that always stuck with you?

TW: First of all, the truth is Martin Scorsese was the reason I did this. Now, people throw that phrase around, “That's the reason.” I saw Taxi Driver, his movie with Robert De Niro, in 1976 when it came out. It was the first movie I saw that I walked out of the theater and went, “What the hell did I see?” That movie was different from other movies. The pacing, the story, the tone, and the ending. It felt different.

I went back and saw it again and again. That movie I can trace to that was the movie that got me interested in cinema as an art form. I said, “Who's this guy? Who made this movie? This guy is Martin Scorsese. What else has he done? He made a movie called Mean Streets. What is he doing next?” That was the thing. Martin Scorsese was the thing that got me going. Several years later, to say, “You are going to meet Martin Scorsese to talk about doing this TV series.” Again, talk about pinching yourself. It’s like, “This is the guy. This is where it all started.”

I'm very happy to say that he is what I hoped he would be. He's a funny, charming, sweet, incredibly, the cinema encyclopedia, warm, welcoming, collaborative guy. As they say, “Don't meet your heroes,” but this is a hero I couldn't have been happier to meet and still this day to call a friend. It's wonderful working with him. In terms of, you say, what advice does he give for a guy who's as incredibly sophisticated a filmmaker as Scorsese? Some of his advice is the most basic stuff.

He will give you notes on things and goes, “I can't hear what the guy is saying. I don't see the gun in his hand. You are not telling me the story. You are not giving me enough information.” It's very basic but you go without that basic idea of, “I literally don't know what's happening.” All the other window dressing is meaningless. His first and foremost, “Can I see it? Can I hear it? Do I understand the story?” It's a good reminder to you, so it's like, don't get too fancy. Make sure you are delivering the most basic version of it, and then we will worry about it.

JE: We have this saying in the news that, “When you mute it, you should be able to see visually what the subject matter is without,” even hearing anything, what they are talking about.

TW: Much information we take in, you don't even realize it's visual and verbal cues. It's funny. I've done that on planes. I've talked about these many times. The idea was that when cinematic became international. It needs to be able to translate into every language. I remember sitting on a flight, and somebody else had a movie on their screen. I was working. Every minute or so, I would look up and watch what was happening on the screen.

This went on for two hours, and I'm pretty sure if at the end of the two hours, you said, “What was that movie about?” I could give you a pretty close approximation of what it was and who's the good guy, the bad guy, and the love interest, and all that happened. It was all visual, and that was by design because that translates to every language around the world. It's not totally dependent on the words.

JE: Wolf of Wall Street, which you wrote, was nominated for five Academy Awards. I know it was a minute ago but congratulations, Terry, honestly. You met Jordan in real-life, and he was incredibly forthcoming and truthful even about the most painful, embarrassing aspects of his life, and there are many. You met with even his ex-wives. You spoke to the FBI agent who arrested him. You had dinner with Jordan's parents. You toured all the different places he's lived. I am curious. After making the Wolf of Wall Street and doing that grassroots, deep-dive research on him. Did your opinion about him as a person evolve?

TW: I didn't ever have a negative opinion of him. My first impression of him I’m reading the book, There But For the Grace of God. Jordan and I are the same age. I grew up in Brooklyn. He grew up in Queens. He was a hustler. He sold Italian ice on the beach as a kid. I was selling bagels at school. We were the same. He worked on Wall Street in 1981. I was a quarter mile away working at Merrill Lynch while he was working at LF Rothschild the day the stock market crashed.

He went to Long Island to sell penny stocks. I went to my law firm and then to LS. Had I met Jordan Belfort in the ‘80s? I very well may have been working with him. I'm not kidding because I was a hustler and a con artist as a kid too. When I read that book, I was like, “I understand this kid.” He was a middle-class kid from Queens who wanted to be successful.”

As he himself said, “You start drawing lines for yourself in the sand.” I'd never do this, and then you do it, and you cross. I will draw another line. Before you know it, you are up to your neck and water. You don't even know how you got there. You add drugs to that equation, money, cocaine, and everything else. Before you know it, you are the Wolf of Wall Street.

JE: You are taking Quaaludes and exploring your way out of a Lamborghini into a country club.

JE: I was fascinated to meet him, and I liked him immediately. He's done a lot of horrible things. He's the first to admit that. He's brought people and done some bad things to his family and hurt people but he is, at his core, a very sweet guy. The more I got to know him, the more I got to see the different aspects of him.

I got to see him as a father and a son and see that sweetness. That's the thing too. None of us is all one thing. Even Tony Soprano has a family he loves, and there are things you have in common. He's a murderer and everything else but no one is all bad or good. If you depict any character in all of their colors, you are going to find things that you empathize with, understand or relate to. Even the worst people will go, “He loves his kids. I get that.”

JE: The scene of Tony jumping into the swimming pool to save his child from committing suicide, that scene did humanize him. There were bits and pieces in there.

TW: You go, “This is a guy who loves his family for all of his faults,” and there are many.

JE: The Wolf of Wall Street, as I said, got nominated for five Academy Awards. I would be remiss if I didn't ask your opinion on the Oscar slap that's heard around the world with Will Smith slapping comedian Chris Rock across the face on live national television. As I'm sure you've seen, Will Smith has been banned from attending the Oscars now for ten years. I have to know, do you agree with the Academy's punishment?

TW: No, I don't think it's severe enough. They should kick him out of the Academy, honestly and take his Oscar away. People say, “What about Lansky and Harvey Weinstein?” They should take their Oscars away too. As much as I've written about violence, I certainly would not condone it in any way and not in a situation like that. The sad thing is if Will Smith had stood up in his chair and said what he said, “Take my wife's name out of your mouth,” and sat back down.

JE: That would have been more powerful than him going up there.

TW: The audience would've applauded and said, “Good for you,” but to walk up and hit somebody. He's clearly got some big issues. The other thing too is the idea that everybody stands up and gives him a standing ovation. I don't think people know what to think anymore about anything.

JE: People don’t know what's reality, and what's fake. I know the chatter on Twitter, people thought it was scripted at first.

TW: People don't know what their core values are. We have been so programmed over the tears years to accept things that are reprehensible as normal that you can watch somebody assault somebody else and then 30 minutes later applaud them as opposed to going, “No, this is wrong.” It's this mass hysteria, mass hypnosis under which the things that used to be career-ending now are getting people elected to public office. People don't know what to believe or what to think. We are losing our ability to rely on our own good judgment about what right and wrong are now. That's a good example. He made a joke. It was a stupid joke. Maybe it was in poor taste.

JE: Both of them were in the wrong, by the way. I love comedians. Chris Rock is awesome. I like Will Smith. He's a talented actor but they both were wrong. I agree with your sentiment. If he had stood up and said something to defend the integrity of his wife, that would have been way more powerful than him storming the stage.

TW: He demeaned himself and the entire thing.

JE: It’s not good. Shifting gears, a lot of people don't know this about you but you wrote 50 Cents’ movie, Get Rich or Die Tryin’. I love that movie. A lot of people do.

TW: You are the only one, a fan I've ever heard. I do not.

JE: You don't?

TW: No, unfortunately, that movie or the script that was shot bears almost no resemblance to what I wrote. It got changed so much.

JE: You are like, “Everyone reading this, that is not a reflection of my work.”

TW: No, it isn't, honestly and I'm glad people like it but that is not the movie I wrote by a long shot. I like to think that what I wrote would have been much better. I think that's born out of its extremely low rating on Rotten Tomatoes. Unfortunately, the script got changed completely by the director, which in the film side of this business, they can do. It got changed into something that I never intended and my name is on it but I don't have any.

JE: A mutual friend of ours shared a rumor and you could either squash this or deny it. I am interested, somebody mentioned something about the first time you met with 50 Cent. He showed up in an alley in an armored car or something. Is there any wild or interesting story you can share about meeting 50 Cent for the first time?

TW: The very first time met him was at a hotel in Santa Monica. I'm trying to think of what year that even was, 2003 or 2002. He was in the middle of some very public beef with another rapper. He was surrounded by security. It looked like the defensive line of the New York Jets. He was in there somewhere and I sat down. When we went on, I was then going to go on tour with them.

As you said before, about the Wolf of Wall Street and I do deep research. I was going to go on tour with them and before the tour, somebody called me up and said, “What size bulletproof vest should we get for you?” It's like, “What? Bulletproof vest?” They said, “You don't want to be catching shrapnel or straight bullet.” I had a bulletproof vest on and we were on tour.

JE: They are saying, “Get rich or die trying, Terry. What can you say?”

TW: That's the die-trying part.

JE: “Art imitates life,” as they say.

TW: That was a little weird but he was great. He was super funny, an incredible storyteller and very forthcoming. He was an open book. The mandate for that movie was to write The Black Goodfellows and I said, “Great.” That's what I did in my original draft. It didn't turn out to be the Black Goodfellows at all. Unfortunately, it turned into something completely different but that was at least what our intention was initially.

JE: You and your wife are considered a power couple in Hollywood. Your wife, Rachel Winter is badass. I have to mention her on this show. She too is an Academy Award-nominated producer for Dallas Buyers Club. One thing I adore about you two is that nothing was ever handed to either of you. You are both such hard workers and you are also a father. If you could leave behind a lasting piece of advice to your kids, what would it be? I would imagine that you and Rachel sit down with your children and talk to them about the values that you've had to learn growing up, having to fight your way to the top.

TW: One of my favorite sayings and we tell this to our kids and try to illustrate is that there is no elevator to success. You have to take the stairs. You have to work. You have to put in the work. You can be handed things but it's not satisfying. It's not going to last unless you do the work and put in the time and the hours.

It's never going to be real and you are never going to respect yourself. Rachel and I were only the second couples in history to be nominated for Academy Awards at the same time for different movies. Originally, the LA Times told us we were the first. There have been many couples who have been nominated for working on the same movie but I wrote Wolf Wall Street. She produced Dallas Buyers Club and that's the thing. The morning it happened, I was in New York. She was at our place in LA and we were on the phone watching the nominations.

My nomination came up first and then the best picture for her. We were like, “If we fantasized about this,” so we talked about this out loud. It would've sounded so goofy, like, “It's never going to happen,” and yet it happened to us. Again, as I said, the hard work, the luckier we get and that’s the same with Rachel. Rachel has hustled since the time she was a little girl. She's still hustling. She's now, as we speak, in Ohio producing the story of LeBron James. A movie called Shooting Stars. It's about LeBron and his four friends growing up in Akron.

JE: Not Space Jam 3?

TW: This is a very different, sweet, poignant story. Rachel, the day we got married in 2009, read an article in Vanity Fair. We are sitting at a hotel pool and she's crying. I said, “What are you reading?” She goes, “This is the best sports story I've ever read. It's the story of LeBron James and his friends.” She said, “I'm going to make this movie.” I said, “If you are reading about it in Vanity Fair, somebody else is probably already making it.” She said, “I don't care. I'm going to figure it out.”

Here we are, 13 or 14 years later and she's making the movie. When Rachel Winter tells you she's making your movie, she's making your movie. She is the most tenacious. She will push a rock up a hill for twenty years to get what she wants and she's done it. I've seen it. Anybody who ever doubts her lives to regret it because she will make it happen.

JE: Those are my people. She's my kind of lady. I can't wait to watch that film. You are the Executive Producer and showrunner of the Paramount Plus Show Tulsa King starring Sylvester Stallone, shot in Oklahoma. You are also developing films and TV for Disney, Warner Bros and HBO Max. I did see something that you are serving as a writer and exec producer of the highly anticipated film the Godmother starring Jennifer Lopez, who will portray the infamous Columbian drug lord, Griselda Blanco. Any juicy tidbits concerning that film that you are able to spill with my viewers and readers? What can we anticipate?

TW: We haven't gotten launched officially yet. I will say that Jennifer Lopez is incredible, big newsflash. Incredibly talented and committed. She is intent on bringing that character to life in a way that is realistic. If you look at the real woman and Jennifer, Jennifer's got a lot of work to do to morph into this film.

JE: Columbian drug lord.

TW: This is great and that's part of what interested her and part of the challenge but it's an incredible story. It's again, in my wheelhouse of crime, violence, and insanity but it will be fun.

JE: Terry, you have quite an impressive resume of people who you've worked with on projects, as I said before. I listed them all, DiCaprio, McConaughey, and Mick Jagger even. Is there any one person who you are dying to work with but you haven't yet?

TW: I would say Al Pacino probably. I'm a huge fan of the Godfather and have been since it came out. He's the one person who's alluded to me not for any other reason that I haven't had a project that he's right for or cast in. He's somebody I've admired forever. I wish there were also certain actors and actresses where I go, “I wish I could take this person and keep them at this age,” where Gene Hackman at 55 years old if they could clone that guy and he pull him out and put him in different things like an incredible movie. Anthony Hopkins, did the same thing. Meryl Streep, it goes without saying. I have been lucky. Listening to you list the people I've gotten to know and work with.

JE: You have to take stock of that. It's a big deal.

TW: If you would've told the fifteen-year-old Terry Winter that, “One day, you are going to be sitting down with Rocky to work on a TV show.”

JE: Tell him to go jump in a lake. I get it. I've never asked this question on my show before but I feel you are the perfect person to ask. I genuinely am curious, if you could name like two people from history to have coffee with, just to shoot around ideas or to even talk about a potential movie script, who would it be and why?

TW: Teddy Roosevelt, one of my all-time heroes. Again, talk about reinvention and I don't know how much you know about the history of Teddy Roosevelt. He came from a wealthy family but this is an incredibly sickly kid who decided he didn't want to be sick and completely transformed his body and his mind through exercise and hard work. Wrote a book on what is the study of bugs etymology or entomology. Whatever the study of bugs is, he did that. At like twelve years old, became a cattleman, the youngest assemblyman in New York State history. The youngest president ever.

JE: Entomology, by the way.

TW: I always get those confused. Ironic is one of them is the study of words. He was the police chief of New York, secretary of the Navy, just a total badass and a fascinating guy. He would be my top choice. Number two, Muhammad Ali, again another hero of mine who is incredible in every way.

JE: Someone asked you a funny question in a previous interview a couple of years ago and I loved your answer. They were like, “Where do you see yourself in ten years?” You are like, “I just want to read a book that has nothing to do with anything I'm writing.” I've never related to something so much in my life because working as a TV journalist in the news, anything I had to read for nearly a decade had to be news related.

As I'm sure you are aware, 99.9% is negative. Zero shortage of negative news these days but I don't know about you. I want to biopic or memoir out of you. I want to see all the nitty-gritty like the 3:00 AM doorman and the butcher shop. I want to see how Terry Winter got to where he is now. Can we expect a future memoir from you or a biopic?

TW: Whether anybody will publish it, I don't know but I'm sure I will write it. It's funny and inspired by Teddy Roosevelt. I keep a journal every day as Teddy did. It's not deep thoughts about things. It's basically what I did that day. I love history. I love the history of my family. I'm the family genealogist. I would kill to have my great, great grandfather's journal from 1850 and what he did every day. I would be fascinated, like, “What do you do when you woke up in the morning?” I went to the blacksmith or whatever it is. I am going to assume that somewhere down the line, I have a great-grandchild who's going to be interested in my dopey lunch at Arts Deli in Studio City or whatever.

JE: We're interested now.

TW: I will at some point write my story down.

JE: Any ideas as to what the name will be? Reinvent it from cab driver to Hollywood screenwriter. From Butcher Shop to the Red Carpet.

TW: Woody Allen’s biography is called Apropos of Nothing, which is great. I have to think about it. I will come up with something.

JE: Terry, it was such an honor having you on Reinvent.

TW: It was a pleasure. I love that you are doing this. I love this idea. This is the thing when I was a kid that I would've listened to get motivated to listen to other people's stories. I love that you are doing this and it helps people listen to you when you are doubting yourself to say, “You can do this.” There are people out there that you can start over, start your path, and go out there and make it happen. We are lucky enough to live in a place and in a country where you can do that. You can basically be whatever you want to be if you are willing to put in the work. As I said before, no elevator. Start taking the stairs and if you got to take them 2 at a time, take them 2 at a time.

JE: There is no greater compliment than that. Thank you so much for that. That's what this platform is for, sharing stories of reinvention and whether you are 70 years old, getting your first book deal or writing your first screenplay, make it happen. You can do it and that's what this show is all about. Thank you.

TW: Thank you so much. It’s a pleasure.

JE: To all my viewers and readers, be sure to rate, review, and subscribe to this show. That's available wherever you listen to podcasts, Spotify, Apple, YouTube, you name it. It's there. That was Terence Winter. Thank you.

Important Links

Terence Winter – Instagram
Martin Scorsese
There But For the Grace of God
Apropos of Nothing
Spotify – Reinvented with Jen Eckhart
Apple – Reinvented with Jen Eckhart
YouTube – Jennifer Eckhart