Gary Gulman and Matt Ruby tape their specials, and I eat a slice abomination.

One Weekend, Two Comedy Special Tapings, and A Third Thing Because Rules of Comedy.

I’m obsessed with words. I never used to be. I wasn’t a reader in school (unless you count Calvin & Hobbes, Animorphs and a hefty dose of Goosebumps). I’ve since found a quiet accommodation with the notion that I’ll never quite ‘master’ the art of writing. Or comedy. But it doesn’t stop me from persisting.

I spent this weekend watching two friends do the single most terrifying thing in stand-up: put words into order, and film it in front of everyone. Two nights, two tapings, two very different styles of comics asking a room full of New Yorkers to laugh on cue, for posterity, before someone yells, “Check the gate!”

Specials used to be rare. There only used to be one every now and then. It was kind of, well, special. Now, there’s a bottomless fire hydrant of comedy specials flooding out of every streaming service every day, and frankly, it’s impossible to keep up with any of them. These days, a special is basically a normal comedy show, except there are giant cameras everywhere, a crane swooping over your head like a rabid seagull, and a producer who has asked you, very politely, to laugh as if a friend’s career literally depends on it. (It does.) Every flub is now permanent. Every cough is now in the mix. The comedian has spent a year or two (sometimes ten) building an hour, and tonight they find out whether it’s a house or a pile of very nice bricks.

Seeing two back-to-back was like going to a wedding on Saturday and then another on Sunday, except at both weddings the groom had to do an hour-long best man speech that killed, and nobody got cake.
(Well. I did get pizza. We’ll get to that.)

In January 2025, through a snowstorm that buried the West Village, I went to opening night of Gary Gulman’s Off-Broadway show, Grandiloquent, at the Lucille Lortel Theatre. I wrote a review so gushing it should have come with a fucking bib.

This past Saturday night, after years of honing it, I watched him tape it for HBO at the Tribeca Performing Arts Center.

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I sat down and immediately spotted my friend Ellis J. Rosen, the New Yorker cartoonist, and his wife Megan across the way. They were flanked by comedians, cartoonists, writers and assorted Manhattan word nerds, the sort of people who will gladly ruin a dinner party by debating the merits of the Oxford comma. Back in January, I said watching Gary was like watching a magician perform in a room full of other magicians who knew all the tricks. This time the magicians brought friends.

He opened with a promise. “I’ll have you out of here by 10:50,” he said. “There’s nothing better than knowing when you’re going to be out of here.” It is the most romantic thing anyone has ever said to a room of New Yorkers on a Saturday night. We all have a train to catch. (We all suspect the train isn’t coming.)

At a taping, the comedian is mic’d for the cameras, not for you. Gary’s voice wasn’t coming through the house speakers, so the whole room leaned forward like a jury straining to hear a witness. For a show about loving words, nobody wanted to miss a single one.

Then, mid-show, someone’s phone went off. This was despite a very explicit pre-show announcement delivered with the urgency of a flight attendant who has seen some shit. Gary stopped and asked, more or less, who the hell was playing Tetris in the middle of the show. What were we doing? Had someone brought a fax machine into the room?

The room fell apart. He’d turned a ruined take into one of the biggest laughs of the night. Later he went back and repeated a few bits for the cameras, which is the dirty little secret of specials: sometimes you’re watching take two. Or three.

It’s a tighter show than the one I saw in the snow. He’s condensed the early days with his mum in Peabody, Massachusetts, including the business of how to pronounce Peabody, Massachusetts, and some of his trademark tangents have been politely shown the door. The whole thing hangs together now, with more laughs and fewer detours, and he didn’t flub a single line. Every syllable was load-bearing.

Seeing a great show twice is a strange experience. You know where the jokes are, and you laugh anyway. Harder, sometimes, because now you can see the joinery.

Then he got to Alan.