Vanessa Hollingshead is a New York stand-up comedian and actress with more than three decades on stage. She trained at the Lee Strasberg Institute, has a Comedy Central special, filmed Showtime’s Funny Women of a Certain Age, and has opened for Richard Pryor and George Carlin.
Nobody at the Comedy Store wanted to open for Richard Pryor. Everyone in the room had come to see Pryor, and Vanessa Hollingshead, a New York comic who had spent night after night waiting in the car park for a spot that never came, was the one they sent up. “I knew they were throwing me to the wolves,” she told us. She killed. We talked about that night, opening for Carlin, the cruise-ship years, and how she learned to “work smarter” instead of getting bitter.
Jump to: From temp to comic · Opening for Richard Pryor · What Carlin taught her · Working smarter · Larger than life · Study everything · Her advice
From temp to comic
Before stand-up, Hollingshead was a trained actress. She spent six years at the Lee Strasberg Institute, on scholarships, preparing for a career in Shakespeare. Then came the day jobs: she worked as a temp in offices on Wall Street during the day and did open mics at night.
Her first real laughs came from that office. One boss explained her job to her slowly, gesture by gesture: “This means hold my calls. This means take a message.” When he went to lunch, she turned to the pool of secretaries and said, “And this means I won’t be coming in tomorrow.” They all laughed. “All of my early comedy that got me my first development deal was all based on real life, working in offices,” she says. Her audience was hard-working people, and she never stopped writing for them.
She grew up in Bed-Stuy, Brooklyn, in the late sixties, “the only white girl, me and my mom, in an all black neighborhood”, with two parents she describes as hippies. Her father was Michael Hollingshead, the man who gave LSD to Timothy Leary and Paul McCartney for the first time, and who was then largely forgotten while Leary got the credit. She is now developing a show about him called The Divine Rascal.
Opening for Richard Pryor
In Los Angeles, the doors stayed shut. “Every night I’d go to the Comedy Store, park my car, wait there for 3-4 hours. They’d never let me up.” Then Richard Pryor came in, and nobody wanted to go on before him. “I knew they were waiting for me to fail.”
She went up with her Bed-Stuy material and her hippie parents. She described seeing a painting of the Last Supper at the Baptist church her mother took her to, with Jesus and all the disciples black except Judas: “I thought it was a picture of the Temptations with their manager.” It worked. Pryor’s bodyguard called her over, and Pryor told her it was great. She knelt by his wheelchair, crying, and told him he was the reason she tried to be so honest on stage.
“I just knew that I was going to be fine.”
Vanessa Hollingshead
Mitzi Shore saw the set, and Hollingshead went from a complete unknown to having her name on the marquee next to Richard Pryor’s. There were no phones to take a picture with. “I will never have a photograph of that and just be in my memory you know in my heart.”
What Carlin taught her
She also opened for George Carlin once, to a very small crowd. She apologised to him for how few people had come. He told her he didn’t mind at all. “I just need to listen to how the words come out.” Decades later, a booker apologised to her for a thin room, and she heard herself saying the same thing. Read more on why Carlin’s comedy has lasted.
When she gets tired of comedy, Carlin is what she goes back to. He was, she says, “a professor and a philosopher about life”. The lesson she takes from him every time is simple.
“Don’t preach. Just tell the truth.”
Vanessa Hollingshead
Her favourite Carlin bit is his routine about religion, the “invisible man in the sky” who always needs money. Ours is his routine on how language softens the truth, from shell shock to post-traumatic stress disorder.
Working smarter
Hollingshead spent almost five years performing on cruise ships, and by the end she found it close to a corporate job. Passengers complained to cruise directors about jokes, and it was easier for a cruise line to remove a comic than to ask them to drop a joke. “We became like the scapegoats in a way,” she says. She started losing jokes and characters, and stayed up at night reading about political correctness, wondering whether she should go back to an office.
What turned it around was something Whoopi Goldberg said: you can let it make you bitter, angry and sarcastic, or “you can just figure out how to work smarter”. She chose the second. Her opening jokes now take on easily offended audiences directly, about a woman offended by her jokes about white American cheese, and a jacket made of “vegan leather”. “Would you skin an eggplant?”
She sees the first 30 seconds of a set as a kind of diagnosis: the drunk guys, the married couple, the girls’ night out, the room that has decided New Yorkers are all liberals. “Being a comedian in many respects is like being a psychologist.” For more on this, read what other comics told us about where the line is.
She is not against sexual material either, only material with no joke in it. Bob Odenkirk’s line about comedians going for “low-hanging fruit” stuck with her, because low-hanging fruit is the fruit that’s rotten.
“I don’t care if you do sexual material but have a punchline. Don’t do stuff for shock value.”
Vanessa Hollingshead
Larger than life
Hollingshead is a physical comic, and proud of it. She grew up loving Lucille Ball, who never minded looking foolish. “If you’re going to do an act out, do it with everything you’ve got.” Selling a new joke with full commitment buys you time while the writing catches up, and no one can steal a bit that only works the way you perform it.
She admires comics who do the opposite, like Todd Barry, who can hold a room with “just straight one line” delivery. She tried set-up, punch, set-up, punch for years and it never fitted. Crowd work is where she feels most at home.
“That’s like jazz. That’s where I get to be free.”
Vanessa Hollingshead
Roasting was harder for her, because she was bullied as a child and found much of it mean-spirited. She did roast Patrice O’Neal, and admires the warmth of Don Rickles, who roasted people without going for the jugular. Women comics, she thinks, still get the harder deal: “we have to work twice as hard to get half the laughs.”
Study everything
People underestimate how much research goes into stand-up. Hollingshead reads, watches and studies constantly: podcasts about Ozempic, looksmaxing videos, beauty trends in South Korea. Her current bit tracks women’s weight loss through the decades, from cigarettes in the fifties to heroin chic, and ends with the men now hitting their faces with hammers to look good. “Welcome to our world.”
After years of “tried and true” material on the ships, being back on land has given her room to write again. She has also taken hot yoga for 16 years, and taught comedy during COVID, which she says brought her back to life when stand-up stopped.
Her advice to new comics
Asked what she would tell a young woman starting out, she did not soften it. Get a thick skin. Don’t take anything personally. Don’t drink with the other comedians. Don’t rely on shock. And educate yourself, because that is where the power is.
“Make yourself undeniable.”
Vanessa Hollingshead
Above all, remember what the job is. For half an hour, the audience is not thinking about the bills, the marriage or the kid who needs rehab. “For half an hour, I’m just going to make everybody forget about their life,” she says. “That’s the gift I’ve been given.”
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For more conversations like this, read how comedians remember their first laugh, or browse all our comedian interviews.