Seinfeld, Louis CK and me: A masterclass in stand-up at New York's Comedy Cellar

New York's Comedy Cellar is the club of choice for the world's best stand-ups. No pressure then, for Andrew Hankinson, as he takes a masterclass and hits the stage for his first (and last) gig.

I wanted to write about the Comedy Cellar, a tiny club in New York that has become the hub of global comedy due to the rise of one of its regulars, Louis CK — creator of his own TV show, Louie, and frequently referred to as the world's best stand-up. The editor said OK, but only if I did stand-up there. For many reasons I should have said no. I said yes.

I arrive in New York on a Thursday evening. I'm due on stage at 4pm on Saturday. It's cold and dark, and I have no jokes. And I don't feel like writing any jokes because when I landed at Newark I read an email from my literary agent saying the book I spent a year and all my money on is not working. I have no savings, substantial debt and a wife expecting our second baby, so I don't want to tell jokes, I want to cry.

I check in to the hotel, call my wife (to give her the bad news) and take the subway to the Comedy Cellar on MacDougal Street, Greenwich Village. I'm meeting Rick Crom, teacher of the Cellar's comedy classes; star of a perfect Louie scene; writer of off-Broadway musical, Newsical. He's going to help put jokes in my material, which is currently just a sheaf of notes I scrawled on the plane. It's probably misleading to call it material.

The Cellar is easy to spot by its famous sign. It became famous like this: the Cellar opened in 1982, survived the 1990s comedy crash, became a favoured venue for Jerry Seinfeld, Chris Rock and Robin Williams, and hit the big time when one of its regulars, 45-year-old Louis CK (a stand-up for nearly three decades), became a superstar sometime between 2007 (when he talked about his children in a stand-up special) and now (he was named one of Time magazine's "most influential people" in 2012, and has won several awards).

Louis still regularly plays at the Cellar (unannounced), which means everyone in the queue asks if he is here, tourists continually have their photographs taken in front of the Cellar's sign (it features in the title sequence of Louie), the club's manager, Steve Fabricant, is offered bribes to let people into sold-out shows (he once declined £300 and was called a schmuck by the Cellar's owner, Noam Dworman), celebrities frequently drop by (Adam Sandler and Katy Perry in the week I'm there), and the buzz is akin to a "hot" bar or restaurant, such as Elaine's in the 1980s. This is where I'll be making my stand-up debut.

I need help. I meet Rick in the Olive Tree, a restaurant above the Cellar, which is also owned by Dworman, who keeps a table permanently reserved for comedians. They sit and eat and watch the TV above the bar, which shows the Cellar stage, while waiting for their slots, at which point they head down the internal stairs. Rick and I do not sit at the comedians' table. He could, I couldn't. Instead, we sit near the window and he gives me two hours of wisdom, sheets from his classes (his students will be the other acts on Saturday) and tips such as "Peel the onion of possibility." Then he asks to hear my jokes.

What I want to tell him is this: "I'm not funny. I'm not a stand-up. Nobody has ever suggested I should be a stand-up. I stopped telling jokes as a child because even then I knew it made people uncomfortable. I fluff punchlines. I mess up deliveries. I once considered trying stand-up but when I mentioned it to my wife she pretended she couldn't hear me. The only time I make people laugh is when I take my top off."

Instead I tell him about a lizard I saw advertising insurance on billboards, television and posters. It reminded me of being in a dictatorship, when you first arrive and notice there are pictures of the local dictator everywhere. The punchline is me speculating that this lizard is America's leader. This is no funnier spoken than it is written down. As I say it to Rick I wrap my notes around my face with embarrassment.

"You can never let the audience know you don't think it's funny," Rick reprimands. I tell him another observation, unfunnily. He repeats it three times in three different ways and it's funny each time. I say I can't do that. He says I just need to craft the joke as clearly as possible. He adds that I can use notes on stage. That's a relief. Then he explains the logistics: he will host the show, I will go on in the middle, where the bad comedians usually go. His final advice: be intimate. "Talk to the audience like you're talking to one person in a bar," he says. "If you can transfer this intimacy to the microphone, that's what great actors do. The only difference is comedians look like we're making this stuff up off the top of our heads, which we're not."

I spend the next two nights down in the Cellar. It has 120 seats, a bar at one end, a bathroom at the other and a stage. Every 15 minutes a new comedian appears. I watch and make notes. Colin Quinn (described by Vanity Fair as a Twitter "master") makes me cry laughing. All the acts are superb and unique. The thing they share, an attribute exemplified by compere, Ardie Fuqua, is charisma.

On the second night I ask Jim Norton (radio host; 30 The Tonight Show appearances; two The New York Times bestsellers) for a closing joke. He gives me one and offers these words of comfort: "You're going to bomb. If not the first time, then the second time. Everyone bombs." I go to my hotel early on Friday night to finish writing. For the past two days I've been transferring my jokes to smaller and smaller cards. I may have been wasting time but I transfer them again while watching Chris Rock on TV. His jokes are better than mine.

On Saturday I get to the Cellar early and talk to Estee Adoram, the club's booker (described as "much-feared" by The New York Times). I ask if British comedians – Jimmy Carr and Jack Whitehall have headshots up in the Cellar – ever struggle at the Cellar due to cultural differences. She says funny is funny. No excuse. Then she asks if I liked Chris Rock. I ask if she means on TV. She says she means on stage last night. Apparently he played a late show while I was at my hotel. That's me bombing as a journalist.

I look over at the TV showing the Cellar stage. The audience is arriving. Estee says not to be terrified. OK. Some of my fellow novices drink a beer before the show. I have seven coffees and the shakes. I walk downstairs and sit in a dark corner. Around 50 people are watching. There are also two babies, surprisingly. The introductory music starts and Rick gets on stage. He tells jokes, plays the piano, everyone laughs and I wish he had set a lower standard. Two comedians go before me and get laughs. I panic.

Then Rick introduces me. The audience claps. I get up on stage. I can't see anybody because the lights are bright. I talk into the microphone. That's a good start. I tell my first joke. They laugh. I tell the other jokes. I get to the end and tell Jim's joke, which is obscene. They laugh. I add an ad lib. They laugh. It's a great feeling, bettered only by the feeling of finishing and getting offstage. Afterwards, two audience members tell me I was good, which I attribute to mental illness, but it was nice of them.

Rick gives me feedback. "The stories were very humorous when you first wrote them," he says. "What you brought to the stage — and I didn't want to make you aware of it — was your natural vulnerability, which is half the battle, because they were on your side before you said anything. You got your big laugh and some applause too, and I saw this sense of relief and joy." Relief, definitely.

Upstairs, Noam invites me to sit at the comedians' table. I watch Anthony Jeselnik (who has his own TV series) read his notes. I get insulted by Sherrod Small. Jim Norton shows me a horrendous text from one of his famous friends. I feel like I belong, for an hour at least. Then the magic wears off, I slow the conversation too many times, and I start to feel like Rupert Pupkin in The King of Comedy. That's OK, I'm an unfunny schmuck, but for five minutes (in my own mind) I was a king at the Comedy Cellar, the funniest place on earth.

Comedy Cellar, New York (001 212 254 3480; comedycellar.com). The original version of this article appeared in 'High Life', available on all British Airways flights (bahighlife.com)