The dynamic between Greg and Patrice O’Neal created some of the most entertaining moments in Tough Crowd‘s history. The two disagreed on many topics and routinely blasted each other, often insulting one another’s appearance and ethnicity. Nick Di Paolo said that “Giraldo let some doozies go on Patrice that only somebody of Hispanic heritage could get away with. He wasn’t afraid to say shit where he could be deemed racist. That’s what I liked about him. He wasn’t very cautious, and I loved that.”

Greg and O’Neal weren’t above focusing on the superficial, with Patrice making fun of Greg’s clothing and hair, and Greg mocking Patrice’s weight. It made for some incredibly memorable television. Here is a sampling of their exchanges:

Patrice: “Here’s why white people are uncool. They’re trying to be black but they still trying to have white style. Like, look at how Colin’s dressed – it’s corduroy, it’s pure trying to be black but trying to keep a whiteness to it. But it fits exactly. Do you see how black people’s clothes, they kind of fit. Now stand up for a second, Greg, just stand one second. You see how Greg’s pants fit? That’s why I don’t like it.”

Greg: “By the way, Patrice, it’s good to see you’ve learned to talk without saying ‘Hey, hey, hey’ first.”

Patrice: “That was a good one, independent-film hair. With your planned messiness. Shut up.”

Greg: “Well, today is a very sad day. I can’t tell whether it’s because of the end of the show, or because of the herd of cattle that died to make Patrice’s coat.”

Greg: “California, for example, had a test, a written test, which was basically a literacy test – and the NRA is saying that’s wrong because there shouldn’t be a literacy test to own a gun. If you can’t read, you shouldn’t own a gun. No offense, Patrice.”

Greg: “Of course blacks watch more TV: there’s not a hell of a lot to do in jail.”
Patrice: “Coming from a Puerto Rican, that really hurts.”

In 1995 Carolines Comedy Club hosted a special event for entertainment executives. It was an industry showcase. Comics would do short sets in hopes of impressing the right people. Greg hated these shows. He considered them a sham to get comics to perform for free. He nonetheless agreed to do this one. Cheryl Bayer from Creative Artists Agency (CAA) was in the audience. CAA was a hugely influential agency. Its clients included David Letterman, Meryl Streep, Brad Pitt, and other A-listers. Bayer watched Greg’s set. She didn’t speak to him afterward, but it wasn’t for lack of interest. She had far greater plans for him.

Bayer walked straight to a Carolines manager and asked, “Is Greg in the Montreal Festival?”

“No,” said the manager.

“Well, he’s in now,” said Bayer. CAA had an open spot at the festival, and Greg filled it.

Greg signed with CAA and flew north to Canada. He took advantage of this opportunity. This was the place where a standout performance could dramatically affect a comedian’s career. Nick Di Paolo said: “In the ’90s at the Montreal Comedy Festival, everybody came home with a deal.”

Rick Dorfman, Greg’s close friend who worked with other Carolines comedians, became Greg’s manager and accompanied him to Montreal.

Greg’s performance at the New Faces show at Montreal Comedy Festival killed. The post-show deal-making began immediately at the bar of the Delta Hotel in downtown Montreal. It was a giant game of cat-and-mouse. Greg’s team strategized to land the best deal possible. Bayer told Dorfman: “When I’m with Greg, come over and I’ll introduce you to whoever I’m talking to. Then leave and come back with some made-up news. If it’s a CBS exec, tell him that some guy from ABC wants to see Greg immediately.”