The Stand-up Set Cycle, From Notebook to TV Special

Ricky Velez in his new HBO stand-up special. Photo: Mark Schafer/HBO

It was early September when Ricky Velez answered the phone and a voice asked, “Where have you been?” The caller was the Comedy Cellar’s booker, and Velez had to fess up. “I have no jokes,” he admitted.

That wasn’t entirely true. Velez had an hour’s worth of his best stuff. But he had just recorded that at Brooklyn Steel for his first comedy special on HBO, Here’s Everything, and when he had reluctantly used that material while opening for John Mulaney a few days later, he regretted it. “I felt like a fraud doing that material again. I wiped out my whole book after that,” Velez recently told Vulture. So he was down to a handful of jokes scrapped from the special and was hanging out, “just waiting to be inspired.”

That Friday, Velez stared at his notes one last time before taking the main stage at the Cellar, the first of his four shows that night. “I was very nervous for the first time in a very long time,” he says. “It’s crazy going back to square one.”

Old-time comics like Henny Youngman, Rodney Dangerfield, and Jackie Mason rode their jokes for years, but it has now become standard practice for top comics to constantly build toward a new special, then ditch their material once it’s done. In fact, while Velez waited until after recording his special to start a new set, other comedians say they start even sooner, jotting down new ideas even as they’re polishing their material for the special so they have fresh jokes and stories ready to go as soon as they’re done filming.

When Gary Gulman, whose last special The Great Depresh premiered in 2019, started in the ’90s, comedians still recycled some material from their specials in their live acts, and creating ten new minutes a year was considered bold. The mind-set was that “you needed to hoard material because it was so precious,” he remembers. Gulman likens the new, unwritten hour-per-year rule to the four-minute mile, which once seemed impossible but then became commonplace. Ronny Chieng — whose last special, Asian Comedian Destroys America, premiered in in 2019 — says it’s challenging, but worthwhile: “You can’t go wrong by pushing yourself as an artist.”

Despite Velez’s concerns, performing material from a special live before the special debuts is considered kosher, Chieng argues, since it allows comedians to work new material in piecemeal, knowing there are guaranteed laughs to balance the set. And jokes that toured but were edited out of a special can live to fight another day. Some get cut for thematic reasons: Gulman’s Great Depresh evolved after his initial hour — with only 15 minutes about his struggles with depression — found no TV buyers. He dropped all other material for a tightly focused show. “I’m proud of that other stuff,” he says, adding that he may return to that other material on tour or even in another special.

But for the most part, comics start from scratch. For Gulman, it’s a solitary struggle since he doesn’t try jokes on civilian friends. “Patrice O’Neal told me never to pimp my friends to determine whether something is funny,” he explains, “but occasionally you’ll say something off-the-cuff funny, and someone will say, ‘You should use that in your act.’” For Chieng, however, bouncing ideas off fellow comedians is part of the process. “I’m not asking people to write entire jokes, but I might ask if a joke goes too far, and sometimes they will add tags to the punch line,” he says.

The real first step is testing new ideas in front of a live audience. Chieng doesn’t write detailed jokes out beforehand. “I’ll think about the phrasing, but I’m not reading it in front of a mirror,” he explains. “I write more in front of an audience than I do by myself.” Gulman used to write out each joke, honing it meticulously in a notebook. But if the joke failed in front of audiences, he felt like he wasted so much time. Now, with experience, he skips those steps in the writing. “I can make a lot of word choices and timing choices intuitively onstage,” he says. “So now, at most, I have a sentence written down, and if the idea works, that’s when I’ll fill the notebook with ideas.”

As new ideas fight for life onstage, comedians need a safe haven to experiment. While Velez just fired away on a Friday night at the Cellar, a favored starting point is the “new joke night.” These are not open mics but shows for established comics to work out material. The Cellar features weekly new joke night shows at its Fat Black Pussycat offshoot, and in 2019, Daily Show correspondent Michael Kosta started Nice Try at New York Comedy Club, a show Chieng says is crucial. “Sometimes I’m just trying to get the words out of my mouth, to see how it sounds,” he says, “and sometimes I’m just tossing out a premise to see if people think it’s funny.”

New joke nights are like training wheels, Kosta says, and his show emphasizes the process to audiences, urging them to be understanding and lower their expectations. “It’s so hard to write a funny bit, and just a little laugh can give us the confidence to keep going with what can become a good bit,” Kosta says. “We can use our years of experience to decipher if they’re genuine laughs or laughs of pity.”

The last 18 months have presented a unique series of challenges for writing new material. For starters, of course, there was the stress. “For a while, I was not thinking about stand-up,” Chieng says. “It was more, If we step out of the house, are we going to die?” Beyond the fear, Velez just felt depleted by the pandemic and found writing without an audience a particular challenge. “I learn about my jokes onstage,” he says.

Gulman was fortunate because he was writing a book over the course of the pandemic, which provided a different creative outlet. He also found certain bits that didn’t work on the page could be saved to adapt for stand-up routines. And Chieng, after resorting to trying to write bits out at home, found his “groove” again working on new material at the outdoor shows in New York’s parks and on its rooftops last fall. In those pre-vaccine days, he found people didn’t want to hear much COVID material but instead were looking for a break: “I could complain about airplanes, even though no one was flying, and they would respond better to that.”

Once new bits are ready, they get incorporated into a 10- to 20-minute club set, but with a cushion, Chieng says. “I open with some new stuff I know works, and then I’ll do the ‘new’ new stuff that you don’t know for sure if it works, and then back to stuff you know works. It’s an old-new-old sandwich.” Jokes that make the club sets are not locked down. “When you know you won’t fall on your ass with it, you experiment more, branch out with more bits related to the core joke,” he explains. As the set grows, comedians start booking longer shows, first in clubs and then on tour in theaters.

“That’s how you really build an hour — doing long shows so you can stretch out and add things,” Gulman explains, adding that he continues consulting with Great Depresh director Mike Bonfiglio on his new material. “He helped so much making it a story rather than just a collection of jokes. Now I still send him recordings as I’m creating my new material.”

Performing longer shows also draws your fans, which Gulman says fuels the material. “The best crowds are the ones that are on your wavelength,” he says. “My quirkiest bits would frequently just die in clubs,” even though those more intricate pieces — like his state-abbreviations bit — “are my best jokes and the ones that eventually got me the most fans. In my head, I had to say, These people are wrong. This is a good routine.”

Out on the road with a new hour, a few stars, including Pete Holmes and Brian Regan, have taken requests or performed fan favorites at the end of sets. Chieng says there’s no single right answer, but he won’t do old bits, because “comedy relies on surprise.” While fans watch specials repeatedly and pick up nuances, he feels old chestnuts lose energy live. (Corporate events are an exception: “Give me enough money, I’ll do pretty much anything.”)

Both Gulman (at Carnegie Hall) and Chieng (Town Hall) have new hour-long shows at the New York Comedy Festival this fall, most of which will be material written since the pandemic … but not all. “There are jokes that survived the pandemic,” Chieng says. “It’s good to see that some stuff I was complaining about before the pandemic is still relevant.”

Gulman was already touring his 90-minute Peace of Mind show a few months after The Great Depresh, but most of that material is now sidelined for his new Born on Third Base show. “One or two stories are thematically relevant and will make it, and other parts might someday work their way into a special or an album, but I really feel like the new stuff is even stronger, so I’m happy to move on,” he says.

After touring the new material, it’s — hopefully — time for another special. “Two years is a really good time to work on a special, but I would say one year is a minimum,” Chieng says.

These days, preparing specials presents one last pandemic-related challenge: to do or not to do COVID-related jokes that may feel dated by the time a show debuts. Velez didn’t want a “time stamp” on his special, so he only brought up COVID once “in passing” during the taping. Gulman is using the pandemic in segues in his new show where it works thematically, and if this tour leads to a special, he’ll retain a few references to give viewers a sense of time while trying to make the comedy as evergreen as possible.

Chieng says he wouldn’t dwell too long on the pandemic in a special, but argues that there’s an inherent value in addressing the moment, as long as you have a fresh angle and funny jokes. Ignoring it completely may actually distract audiences, he argues. “Are we going to pretend it didn’t happen? Isn’t that worse?”

Eventually, as Velez is now learning, after a special is filmed, the cycle starts over immediately — a blank slate, a new hour to fill. “It is so daunting,” Velez says. “How do I top what I just did? There’s more pressure now.”

After The Great Depresh debuted in 2019, Gulman got a call from producer Judd Apatow. “He said, ‘You do not have any obligation to top it or equal it,’” Gulman recalls. “That was such a relief because there was a letdown after I taped it and another letdown after it aired. My thought had been, What do I do for an encore?

The Stand-up Set Cycle, From Notebook to TV Special