The Art and Anxiety of Booking a Hit Comedy Showcase

Marianne Ways has booked showcases of stand-up comics like Night Train With Wyatt Cenac and now Butterboy.

Soon after Marianne Ways arrived at her office one Monday morning this month, she called to check on sales for that night’s performance of Butterboy, the weekly showcase of stand-up comics she produces at Littlefield in Gowanus, Brooklyn. Then she started worrying.

Only 26 tickets sold. The space fits 250. “That sucks,” she said by phone, and not only for business reasons: a sparse crowd gets self-conscious and is hesitant to laugh. Ms. Ways, 37, has been putting together comedy shows long enough to know she would have to come up with a quick fix.

Part of what makes New York the greatest city in the world to see live comedy is the large number of cheap, easily accessible and impressively curated live shows outside the clubs. These were once considered alt comedy; now some (Whiplash on Monday, Sweet on Tuesday) are institutions. Their hosts may get the applause, but the far less well-known bookers are the crucial players who establish the vision and quality control. To understand the art of her job, I followed Ms. Ways for one week, keeping in touch by email and phone to see what went into putting together a lineup.

Ms. Ways is one of the most important gatekeepers in Brooklyn’s fertile stand-up scene, which is centered not in clubs, but in bars and performing spaces like Union Hall and Bell House. She first established her reputation in the borough in 2010, booking Hot Tub, which was created by the hosts Kristen Schaal and Kurt Braunohler on Monday nights. When that popular show moved to Los Angeles, Night Train, which she created with the host Wyatt Cenac, took over the slot. As soon as it ended in November (Mr. Cenac will have a show on HBO), she started Butterboy with three new hosts, Jo Firestone, Aparna Nancherla and Maeve Higgins. All of these became popular hits, sharing the same diverse aesthetic, progressive vibe and balance of famous names and new voices.

Ms. Ways — who grew up in west Pennsylvania more of a music fan, but became seduced by the comedy of the sketch series “The State” — now books three shows, including ones starring David Cross and another with Sasheer Zamata, but describes them as labors of love. She earned $10,000 from Night Train last year, and said Butterboy will probably bring in less. She makes her living from a company that puts on live events.

She had been trying to move away from headliners, drawing audiences based on her show’s reputation as a home for stellar comedy. “You don’t need an hour special on HBO to be great,” she told me the week before, and that is undeniably true. But sometimes, you do need someone with major credits to fill seats and avert disaster. Factoring in time needed for promotion, she had mere hours to track one down on this particular Monday.

There is not only an art to putting together a lineup, but also a politics, especially now, when issues of representation (Ms. Ways always books at least two female comics) and sexual misconduct have roiled the comedy world. Should Louis C.K. and Aziz Ansari return to live stand-up, the first people confronted with a difficult choice will be bookers. Ms. Ways said she would check with her hosts, but probably wouldn’t book Louis C.K., but likely would Mr. Ansari. Then she paused. “I don’t know,” she said. “I have very mixed feelings on his situation.”

Ms. Ways had already booked the core of her show a week before, with regulars including Seaton Smith, a reliably funny comic, and Eman El-Husseini, a lesbian Muslim stand-up with punchy, wry jokes about identity. She also signed up Leah Bonnema after seeing her perform at a festival, and a comic whom she had never seen, Chris Duffy, but who had come recommended by her hosts.

Much of her time is spent figuring out the right order of comics, a process she describes with a strategic eye. Newcomers or comics who do particularly provocative work that might go wrong are slotted in the middle, and she tried to follow with someone who would kill. She knew Mr. Smith would deliver a crowd-pleasing set so she scheduled him last. She focused more on mulling over the right opener.

It’s essential to start the show with the strongest or second strongest comic, she said, preferably someone with high energy. “Leah is more a storyteller, which might mean a slow build, so I wouldn’t start with her,” Ms. Ways said, preferring to begin with someone who gets laughs fast. “That leaves Eman. She has great energy.”

The previous week she had checked her inbox for videos of young comics who could fill the guest spot, which was four minutes shorter than the other 10-minute sets. Two stand-ups were just O.K., but she really enjoyed a young comic named Mara Wiles and signed her up. Ms. Ways said she liked the balance: high and low energy, emerging and established, a range of demographics.

But come Monday, what was still missing was a headliner. Her hunt began by scouring late-night television guest lists. Wanda Sykes, whom she has never booked, was in town for “The Late Show With Stephen Colbert.” Showcasing her would be a coup, but Ms. Ways reconsidered in light of the low presales: playing in front of a small crowd would be a terrible way to introduce Butterboy to Ms. Sykes. Then she turned to go-to stars. Jim Gaffigan had just performed last week at Butterboy. Mr. Cross, who has a baby girl with his wife, Amber Tamblyn, would probably be busy with child care (she tried anyway; no luck). She contacted Mr. Cenac, Michael Che, Todd Barry, Janeane Garofalo, Mike Birbiglia, Roy Wood Jr. and Phoebe Robinson.

As she does most weeks, she texted her friend Jeremy Levenbach, who books Whiplash at Upright Citizens Brigade, which generally showcases more headliners. Their brainstorm led her to contact Jon Glaser and John Hodgman, both unavailable.

By 2 p.m. Monday, the day of the show, when she hoped to be promoting it online, Ms. Ways had heard only polite rejections, and started striking a different tone. She said her anxiety was fading as she accepted that her lineup was good enough. Minutes later, Mr. Cenac and Mr. Che said they couldn’t do it, and Ms. Ways said, “I haven’t struck out this much since I was on the softball team in third grade!”

Roy Wood Jr., a “Daily Show” correspondent and host of the Comedy Central series “This Is Not Happening,” had still not responded, but with four hours before the show, Ms. Ways thought a text might have more luck; she sent a message saying she needed “star power.” Within a minute, Mr. Wood responded that he was in. She had her social media intern, an aspiring booker herself, post the news on Facebook and Instagram. In the next hour, ticket sales rose to 46, still dangerously low.

Ms. Ways arrived at Littlefield an hour early and ordered pizza for the comics, who earn $30 apiece for performing. She shares her cut of the door with the hosts. When the comics arrived, Ms. Ways greeted them warmly, a hurricane of energy, complimenting outfits, doling out hugs and cracking jokes to keep the mood light. Backstage she was relaxed. Out front, she was more tense, checking her phone and eying the crowd warily. “I don’t like to see these,” she says, pointing out empty chairs, of which there were a few. With walk-ins, the final count was 103.

Onstage, after Ms. Firestone bantered charmingly about her bat mitzvah with her co-host, Ms. Higgins (Ms. Nancherla was out of town), Ms. El-Husseini opened strong with honed religious material about being a Muslim married to a Jewish woman. It’s much harder to convert to Judaism, which, she joked, had higher standards. “Jesus Christ wasn’t good enough,” she added. “Those are standards.”

Ms. Ways raised her cellphone to indicate the comic had two minutes left. She told her last joke and exited precisely on time. “She’s a pro,” Ms. Ways said.

Mr. Duffy did a tight set, followed by Ms. Wiles, who was more hit or miss. “She’ll get there,” Ms. Ways said. After a last-second addition — Yedoye Travis, who said his name translates to “African-African dad’s from Florida” — Mr. Smith got ready to go onstage. Mr. Wood was to follow him but had not shown up. Ms. Ways did not seem worried, and sure enough, just as Mr. Smith began, Mr. Wood walked backstage.

Mr. Smith dipped his toe into sexual harassment material — “All men are creepy until proven not creepy” — to muffled response, then moved on.

Mr. Wood did some #MeToo material with more success, analyzing apologies from disgraced men. “The only person who did it right was Bill Cosby,” he said to dead silence. “They hit him with allegations, and he went blind.” The huge laugh built into a roar as the rest of the set went long, nearly 20 minutes. This night ended with a kill, and the sound in the room made it feel packed.

At the show, Ms. Ways seemed relieved: “I spend the day worrying to solve problems before they happen,” she said.

Her post-mortem the next day, after the final numbers came in, was more balanced, conceding that a fifth of the tickets were comps. Still, they laughed loudly. “They were small,” she said, “but mighty.”

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