From I Love Lucy to The Sopranos

By Paul Parcellin • October 26, 2021

The paths writers take toward achieving their career goals are varied, and Terence Winter’s passageway toward television writing included detours into medieval history studies and becoming an attorney—the latter he decided he could do without. His passion for history stuck with him, and no doubt helps fire the creative flames in producing the HBO series Boardwalk Empire, of which he is showrunner. Set in 1920s Atlantic City, N.J., the multiple, Emmy Award-winning series chronicles the bootleg liquor business that sprang up during Prohibition.

At first, Winter’s creative impulse was not focused on crime, but on network sitcoms. To that end, he is a mostly self-taught writer. “It helped having already watched a billion hours of television as a kid,” he says. But he did not take the plunge into writing until he was around 30, after a couple of career false starts. “I already sort of knew what a sitcom sounded like. I probably paid a lot more attention than the average viewer of how shows were structured, how jokes are set up and paid off.” He grew up in Brooklyn, N.Y., in the 1960s and 1970s, and he stayed glued to a local channel, WPIX, that re-ran many of the notable sitcoms from the 1950s and 1960s. He maintained a steady diet of Father Knows Best, The Honeymooners, I Love Lucy, My Little Margie, F-Troop, The Munsters, Gilligan’s Island and Abbot and Costello, which were played time and again. “It was so drilled into my head. Every comedy routine, every setup and payoff ever written, so when I sat down to teach myself how to do this I knew what a sitcom looked like and how it should plot out.” However, sitting down and putting ink to paper proved to be a bit more challenging than plotting out stories in one’s imagination, so he went out and bought TV show scripts to read. “This was back in the pre-Internet days, and you literally had to buy scripts from a guy on Hollywood Blvd., selling bootleg copies of existing scripts to see how they were formatted. I bought Syd Fields’ book Screenplay and devoured that.” Then, he began “dismantling” TV shows, much like a curious electronics enthusiast who takes apart and puts together a radio, reverse engineering it to discover how all of the tubes and buttons work. He taped shows, such as Home Improvement, on a VHS recorder, and then watched, stopping the machine to write down what happened in each scene to learn how the writers set things up, how they set up the problem that would drive the action in the first scene. He noticed that in episodes of Home Improvement, right after the commercial, the show’s star, Tim Allen, always talked to the guy over the backyard fence, and viewers got a piece of information there that would set the episode’s gears in motion. He analyzed shows this way for several months, approaching it as if it were a full-time job. Then, he wrote a Doogie Houser spec script.

He had moved to the City of Angels without knowing a soul, a prospect that might strike fear into the hearts of those from the hinterlands, but it proved to be a productive and uplifting experience for the aspiring screenwriter. “I highly recommend taking yourself out of your comfort zone,” he says. “One day it occurred to me, trying to write and make phone calls to agents would be so much easier if I lived in Los Angeles. It was like, Duh!, move to Los Angeles.” His entire life had been centered in New York, so leaving friends and family behind was a big step. “I’d wake up every morning and think, where am I? In Los Angeles. What and I doing here? Oh, yeah, I’m trying to be a writer. It really put a fire under my ass.” Suddenly living in a strange place with no family and friends, and no distractions was uncomfortable, he admits, but ultimately exhilarating and freeing. “It made me want to do it even more.”

Once settled in L.A. and writing, Winter got down to the daunting task of marketing himself as a writer. Producers shunned scripts from unrepresented writers, and agents wouldn’t read his work, either. Out of desperation, he created his own agency. He got a list of agents who were receptive to unrepresented, unproduced writers, and he noticed a familiar name on the list. It turned out that this was a guy he went to law school with. He had a client who wrote a book on real estate, and he used his fee to get bonded as an agent, but was not representing show biz clients. Winter cut a deal with the guy—he let the aspiring screenwriter submit his work under the lawyer’s letterhead, and he agreed to split any earnings he realized from script sales. A Mailboxes Etc. on Santa Monica Blvd. served as his agencies mailing address. He bought letterhead, got a phone mail system and started getting his work out to prospects. He then had an agent, at least on paper, who represented him, so he could submit his work to various TV shows and production companies without his scripts coming back in an unopened envelope. A big part of getting started, maybe almost as important as the writing itself, he says, is being able to get people to read your scripts and focus on your work. “It’s 50 percent talent, initially, and 50 percent selling yourself. No one has ever knocked on my door and asked to read a script of mine.” He concluded that if you’re not getting your work out there, you could be the greatest writer in the world and no one is going to see it. However, self-promotion is only effective if you practice it with a sufficiently light touch. “It’s a really thin line between being a pain in the ass and being assertive,” he says. “And you’ve really got to know where that line is, because you can become really obnoxious and offend people, and piss people off. Or, people can say, all right, this guy’s just trying to get out there and get read.”

In 1994 he landed a spot in the Warner Bros. TV Writers’ Workshop, focusing on sitcom writing—Warner Bros. also runs a workshop for a drama writers. Each year, up to 10 participants are chosen from nearly 2,000 applicants. Once you’re in the program you are exposed to writer and showrunners working on a Warner Bros. televisions show. You write a spec script, and the goal is to get all participants staffed on Warner shows by the end of the 10-week program. In addition to Winter, some of the program’s other distinguished alumni includes Marc Cherry (Desperate Housewives), Greg Garcia (My Name Is Earl) and Felicia Henderson (Soul Food). Things worked out well for Winter, but not in the way he expected. He wrote a Frasier spec, which was well liked, but the writing program staff had an alternative path in mind for the fledgling writer. He learned that they hoped to connect him with a one-hour drama that also had comic elements. The show focused on a blue-collar lawyer who goes to work for a very stuffy law firm—a mirror image of Winter’s background. He grew up in Brooklyn, in a working class environment, went to law school and was hired by a stuffy Manhattan law firm. “They (Warner Bros.) said, you think you can write this? I said, if I can’t write this I’m getting on a plane and leaving.” So The Great Defenders became his first staff writing job. It was there that he met Frank Renzulli, who co-created the show, and later went on to become one of the first writers on The Sopranos. It would turn out to be a significant meeting.

Winter held a series of varied writing jobs over the next five years that included Flipper, Xena: Princess Warrior and Sister, Sister.

When The Sopranos premiered in 1999, Winter says he was on the sidelines watching it in awe. “I was thinking, this was the greatest TV series I’ve ever seen.” Upon watching the pilot episode, he called Frank Renzulli and said, have you seen this thing? “He said, yeah, I’m meeting with (Sopranos creator) David Chase on Friday. I said, you’ve got to get me in there.” But it turned out that Renzulli was the last writer Chase hired. “So, every day Frank was going to work he’d call me at the end of the day; he’d tell me about the writers room, and he’d email me scripts and scenes that they had written, and I was editing his work and giving him suggestions. So, I was sort of working on the show even when I wasn’t.” Winter recalls being blown away by Renzulli’s writing on The Sopranos. “It was so much better than anything he’d ever done before, because it was real, and it was his real voice. And for me, that’s what made a difference. This was not writing with handcuffs on.”

Back then, with Winter’s sitcom-heavy resume, it was an uphill battle persuading Chase that he could take a place at that show’s writers’ table. But Renzulli stepped up to the plate for him. Winter says that both he and Boston native Renzulli came from similar backgrounds. “He very much understood the world that he was writing about,” says Winter, “much more so than I even did.” However, growing up in Brooklyn, Winter was hardly unfamiliar with the kinds of guys who filled out The Sopranos cast. He got some on-the-job training in wiseguy culture in the early 1970s when he worked for former Gambino crime family boss Paul Castellano in his Brooklyn butcher shop. “There were a lot of track suits and pinky rings,” Winter recalls.

Chase was hiring more staff for Season 2, and Renzulli recommended Winter for the job. “Nothing I had written up until that point gave any indication that I could do the show,” he says. “It was really Frank’s insistence … he just knew in his heart that I could do it, and David took a leap of faith and let me write an episode, and it worked out. And I wrote an episode, and he offered me a permanent job on the show.”

Winter says not much has changed for new writers these days. “So many people want to do what we do. And this business is attractive to people who are talented, and un-talented. Everyone thinks that he can write a script. And I think a lot of people severely underestimate the work that goes into this, and the fact that this is a craft and it takes years to learn.

“So, you’re competing not only with other talented people, but also the masses of untalented people who are writing scripts and submitting them. Agencies and production companies get inundated with paper and emails. It’s really hard to stand out, even if you’re talented.”

The complexity of the business also presents obstacles to the aspiring screenwriter. “So many things have to go right in order for a showrunner or producer to pick your script out of a pile, read it, like it, pick up the phone, call you, have a job for you or have money to spend on your script.” Given those circumstances, many writers might conclude that they have a better chance of getting hit by lightning than being discovered and hired. “Maybe you do, but you’ve got to persevere, keep doing the work, keep networking, keep getting out there, again, without being too much of a pain in the ass, and try to get your work read.”

So, how does one break in? There is no one path or set of steps. “If you asked me how to be a dentist I could tell you the four things you need to do to become a dentist. How do I become a professional screenwriter? I don’t know. There are a lot of different ways to skin that cat, but I do know that all of them entail writing a lot and not giving up.”

Paul Parcellin