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Top New York Comedy Writers Tell How to Start and Sustain a Career in Comedy

Top New York Comedy Writers Tell How to Start and Sustain a Career in Comedy

On Tuesday, five of the city’s best comedy writers took the stage at the small Triad Theater on the upper west side as part of New York Comedy Festival. Alan Zweibel, (“SNL,” “It’s Garry Handling’s Show,” “Curb Your Enthusiasm”) moderated the panel, which included Andy Breckman (“SNL,” “Monk”), Michelle Wolf (“Late Night with Seth Meyers”), Matt Roberts (“Late Show with David Letterman”) and multi-hyphenate writer of screenplays, essays, novels and plays Delia Ephron. The panel represented a diverse group of comedic talents working in a range of forms, with aspects of their craft spanning across writing, producing and creating television shows, as well as films and novels. 

READ MORE: 7 Films That Get Serious About Stand-Up Comedy

The panel’s approach was light overall, making audiences laugh with their banter and tales of show business. Everyone involved was nonetheless eager to share their advice about how to break into comedy and how to sustain a career in an ever-changing industry once you get there. Here are some of the highlights:

“Be ready to get lucky.”

In sharing their stories of how they got started in comedy, one thing all the panelists had in common was that their careers were jump-started by a meeting that happened more or less by chance. Matt Roberts became a segment producer for “Late Show With David Letterman” 23 years after landing an internship with the show, slowly working his way up the ranks: When he was still at school, Roberts was involved with a committee that brought frequent Letterman guests Penn and Teller to campus with a show, and after making a good impression and having lunch with Teller, he convinced the magician to write a letter of recommendation that won him the position.

“Late Night With Seth Meyers” staff writer Michelle Wolf was working in the finance and tech industries while doing standup comedy in the city, but ultimately it was her Twitter feed that got her the job. Her social media presence got the attention of a staff writer for the show, who asked her to write a packet (a late night comedy version of a writing sample, with sketches, monologue jokes, and desk pieces). After an interview that lasted only ten minutes, Wolf was sure she’d blown it, because as a former recruiter for a tech firm, she was used to a successful interview lasting for most of the day. She was surprised when they called back a few weeks later, offering the job.

Ephron was destined to be a writer based on upbringing alone: Born to screenwriter parents Phoebe and Henry Ephron, Delia and her sisters Nora, Amy, and Hallie had literary ambitions forced upon them. “All my mother wanted was for us to be writers. That’s all she cared about.” Ephron said of her childhood. “Every time I said something funny my dad shouted ‘that’s a great line, write it down!’ Or my dad would say ‘That’s a great title,’ so I have titles with nothing to go with them.”

In terms of own career, it began with a bowl of pudding. “I was down to like 300 dollars, and I was sitting down eating chocolate pudding,” she remembered of a time when she was trying desperately to get published in the New York Times, “And I thought, I’m eating like a child. And I wrote 500 words called ‘How to Eat Like a Child.'” In under a week, she had a book contract.

Breckman’s opportunity came when his manager submitted his rejected “Saturday Night Live” packet to “Late Show With David Letterman” on a long shot without telling him. He was working at a video store when the phone rang, and he picked up to hear that his manager had gotten him a once-in-a-lifetime opportunity to meet Letterman while he was in New York looking for writers. The catch was that he would only be in town until the next morning. Breckman raced home and hand wrote his Letterman packet in one night. “I needed my wife to wake up and type it up,” he said, remembering a time before the computer age, where typing was not a universal skill, “it was four in the morning, but I turned all the clocks in the apartment to say 6:30 so she wouldn’t be mad at me.” Breckman then raced back uptown to deliver the packet that got him his big break.

In the case of the moderator, Zweibel’s first “professional” writing experience was working at a deli and selling jokes to comedians working in the Catskills for $7 each. The first joke he ever sold was about a sperm bank: “‘It’s just like an ordinary bank except here when you make a deposit you lose interest.’ I then became the sperm bank guy up in the mountains.”

Eventually, Zweibel took all his unsold jokes and turned them into his own standup comedy act. Four months into his standup comedy career Zweibel had just finished bombing when someone came up to him and called him the worst comedian he’d ever seen. He then told Zweibel that his jokes weren’t bad, and asked if he could see them. “And I agreed, I said sure. I didn’t even ask who this was. I would’ve shown it to a gardener at this point. And it turns out this is Lorne Michaels.”

The legendary SNL creator was in the city looking for writers, and Zweibel went home and wrote a packet of over 1000 jokes. Before long he was a founding writer of “Saturday Night Live.” Zweibel described the unusual ways they got in the door as a testament to their “cunning,” but Breckman suggested that “you have to be ready to get lucky.”

When you’re writing jokes, remember who you’re writing them for.

This is advice that applies to characters in TV, film or novels, but more importantly to writing for the host of a late night show. Late night hosts have a distinct voice, and most viewers don’t want to break the illusion that the star has a staff of writers giving him material. This means your jokes need to be more than funny, they have to be right for the performer. Wolf has run into this problem, where great jokes for her own standup wouldn’t work for Seth Meyers. “This is going to sound bad coming out of a young white man’s face,” she said of that type of material. “He’s going to either sound terribly misogynistic if he says this. I could do that joke, that’s a good joke for me.”

Zweibel gave his own technique for helping to develop specific voices. “I’d pick a week, say this week is ‘buying a car.’ Monday, I’d write a monologue the way Jack Benny would say it, about buying a car. Tuesday, it would be Richard Pryor how he would say it, Wednesday Joan Rivers, Thursday David Steinberg, Friday Rodney Dangerfield.” Zweibel practiced this way to train himself for writing scripts, to make sure his characters wouldn’t sound alike.

There’s no easy fix for writer’s block.

At one point in the panel an audience member asked them the eternal question: “How do you cure writer’s block?” The panelists’ silence (broken by Breckman jokingly responding “masturbation”) spoke volumes to the fact that there simply is no easy fix for getting stumped. Ephron remembered the advice of her “shrink,” who told her to “sit down at 10:00 and don’t get up until 12:00. Sit down at 2:00, don’t get up until 4:00. You can’t make tea, you can’t make coffee, you can’t feed a plant, you can’t feed an animal, you literally just have to sit there. And you will write.” Through enough discipline, these rules will eventually become habit. 

Along the same lines, Wolf spoke to the fact that writing for a daily show forces you to write every day whether you want to or not. In this situation writer’s block isn’t just an annoyance, it’s a job hazard. “There’s just some days you’ll just be staring at your computer and you have to come up with something. It might be total garbage… but you have to do it.”

In Roberts’ experience, it can be constructive to break down the problem into its mechanical parts. “You almost do it in a more scientific way than an artistic way, and then eventually something will trigger you and you’ll go ‘oh, wait, but this would be funny,’ and then the art enters back into it. For me, that was always the trick.” 

Zweibel found difficulty transitioning away from the lively writer’s room at “SNL” into more solitary writing. “A TV show is totally social. It’s who you want to be with, it’s who’s around the table, and what are the different sensibilities. There’s a certain synergy there which is really cool. You go from that to writing by yourself, you’ve got to make up for that kind of energy somehow.” His own fix is to be working on multiple different types of projects at once, and if he’s stuck on one he’ll jump to another and reset. 

Find your own voice.

While you have to have the ability to write for other people, it’s important that you be able to distinguish yourself from the crowd with your own unique perspective and voice. The panelists agreed that it’s important not to let your own voice be buried under the voices of those who influence you. “I think we inherently start off writing for a voice we really like,” Zweibel noted, thinking of how he and other people coming up in comedy around the same time sounded just like Woody Allen when they were starting off. 

Ephron feels every writer will naturally develop their own voice over time, but it might take some time to isolate it. “I think probably everybody has this moment where you suddenly write the thing and it tells you who you are in a bigger way than just as a writer.” 

Broaden your skill set to lengthen your career.

At the time of the panel Alan Zweibel discussed three current projects in different mediums: a play, a musical, and a novel. The ability to wear all these hats has given him the ability to continue his comedy writing career long after leaving “SNL.” In fact, everyone at the table was a multi-hyphenate in some capacity, expanding their comedy craft through standup, songwriting, novels, plays, and more. This ability to flex different “comedy muscles” gives them the ability to be versatile and avoid getting boxed into only one role. This also allows writers to use the technique Zweibel described above, rotating between projects as a cure for writer’s block.

“I’ve certainly had gigantic flops,” Ephron remembered. “You can end up in screenwriter jail or something. So then I would go write a book, and someone would option it. So in thinking of your career, don’t just think of it in one way. Try to develop other areas.”


Learn to expect rejection. 

It’s no secret that getting started in any creative field involves a long process of near-constant rejection. The bad news is, that rejection never stops. At “Late Night With Seth Meyers,” Michelle Wolf might write a hundred jokes for the monologue and have only two of them make the cut. 

And even after winning an Emmy for “Monk,” Breckman finds that “not a day goes by where somebody doesn’t pass on something I wrote or reject something I wrote. Every day somebody’s reading a script and deciding they don’t want to act in it or direct it. You can’t take it personally.” 

Don’t wait to start writing.

A symptom of being a young writer can be to keep waiting for your “big break,” or that “get lucky” moment the panelists experienced, to really start writing. While it’s easy to feel overwhelmed and discouraged by the difficulty of finding a job writing comedy, it’s important not to wait for that job opportunity to start honing your craft. “What we don’t have as writers unless we do it for ourselves is have control,” commented Zweibel, “and the only way we can maintain control is by creating as opposed to waiting for the phone to ring.” 

READ MORE: How To Write For TV: ‘Brooklyn Nine-Nine’ Scribe Laura McCreary Shares Her Secrets

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