Greg Giraldo: A Comedian’s Story

A book about one of this century’s best comedians.

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About The Authors

Matt Balaker and Wayne Jones

Matt Balaker is a comic, writer, and former investment fund manager. He lives in Southern California with his two boys and one wife.

Wayne Jones is a writer, editor, former academic librarian, and a big fan of stand-up comedy. He has published stories, articles, novels, and non-fiction books, and maintains a blog and podcast. Wayne lives in Ottawa, Ontario, Canada.

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Greg Giraldo: A Comedian’s Story

Learn Greg Giraldo’s story from those who knew him best.

Many know Greg Giraldo’s work from Comedy Central roasts, late-night television, and comedy clubs. However, few comedy fans have heard the story of his days after Harvard Law School, ascension to cult comic icon, and premature demise from his addiction. We’ve interviewed over 60 people who help tell his story. From managers to his former wife, and many comedians, friends, producers, and entertainment journalists and writers — all to uncover what motivated this stand-up legend and the impact of his work.

The book is now available!

Available as a paperback, ebook, and audiobook. Enjoy all three formats if you like!

Events, Interviews, Media

  • June 13, 2016: Interview of Matt Balaker by Sean L. McCarthy on The Comic’s Comic site
  • Dec. 19, 2018: Interview of co-author Wayne Jones on CKCU radio: here (click “Listen Now”: begins at 1:07:50)
  • Jan. 15, 2019: Interview of Wayne Jones on Media Whore blog
  • Feb. 4, 2019: Interview of Wayne Jones on Daytime Ottawa with Dylan Black at 1:00 pm
  • Mar. 8, 2019: Comedy show and book signing with Matt Balaker, Winston’s Ocean Beach at 7:00 pm
  • Mar. 20, 2019: Reading, Q&A, and book signing by Wayne Jones, Yuk Yuk’s, Ottawa at 10 p.m. (details here)
  • Mar. 25, 2019: Interview of Matt Balaker on Jeff Ross’s podcast, Thick Skin, along with Jesse Joyce
  • Mar. 27, 2019: Interview of Matt Balaker by Teme Ring on Comedians Defying Gravity
  • Mar. 28, 2019: Book signing and discussion with Matt Balaker, Book Soup on Sunset in W. Hollywood at 7:00 pm
  • April 16, 2019: Interview of Matt Balaker on Ted Alexandro’s A Little Bit Me podcast
  • May 5, 2019: Interview of Matt Balaker on the Roadstories podcast
  • June 10, 2019: Interview of Matt Balaker on Adam Carolla’s podcast, Take a Knee (subscription required)
  • June 11, 2019: Book launch and signing at the Fat Black Pussycat (sister club of the Comedy Cellar), with both authors, New York, NY
  • June 11, 2019: Matt Balaker (and, later, Wayne Jones) on the Comedy Cellar’s Live from America podcast with Noam Dworman
  • June 11, 2019: Matt Balaker and Wayne Jones on the Comedy Cellar’s Live from America podcast with Hatem Gabr (YouTube)
  • June 12, 2019: Interview of Wayne Jones by Dustin Chafin on his I’ll Leave You with This podcast
  • Aug. 20, 2019: “One Tweet from the Right Person,” Media Whore Blog
  • Sept. 20, 2019: Interview of Matt Balaker on The Caregivers podcast
  • Sept. 23, 2019: Matt Balaker and Wayne Jones talk about the book on OLA’s Open Shelf magazine’s SoundCloud
  • Dec. 9, 2019: Interview of Matt Balaker by Kerri Edelman on her show
  • Dec. 22?, 2019: Reviewed by comedian Barry Mitchell on ABC TV’s World News Now (vimeo here)
  • June 16, 2021: Matt Balaker interviewed on the Honest Offense podcast with Eric Cervone.

Reviews and Excerpts

Excerpt from the chapter on Tough Crowd

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.”

Excerpt from the chapter on Common Law

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.”

Excerpt from the chapter on the roasts

From 1998 to 2002, Comedy Central aired five Friars Club roasts. After five years, the agreement between the Friars Club and Comedy Central ended. In 2003 Comedy Central inked a deal with Denis Leary’s production company Apostle. Frank DiGiacomo reported: “Though the partnership had been extremely lucrative to the Friars, they seemed relieved to be free of the yoke of national television. No longer did they have to lard the dais with young observational comics for the sake of demographics, or deal with big-name comedy stars who were afraid of working blue on national cable television.”

The first of the revamped Comedy Central roasts aired in 2003. Robert Kelly traced the origin of these shows to a roast of club owner Barry Katz that took place at the Boston Comedy Club in New York: “Jeff Ross sold the idea to Comedy Central. It was just us celebrating each other and smashing each other. It was pretty fucking great. It was at a little club, just us, mostly comics. Some industry, a little fans. To me, it’s what roasts are all about.”

Greg performed in nine of the roasts that aired on Comedy Central: Chevy Chase in 2002, Jeff Foxworthy and Pamela Anderson in 2005, William Shatner in 2006, Flavor Flav in 2007, Bob Saget in 2008, Larry the Cable Guy and Joan Rivers in 2009, and David Hasselhoff in 2010. Comedians and comedy fans revere Greg as one of the best roasters ever. His intelligence, writing skills, ability to ad-lib, and his lack of concern for being offensive all came together. The results were often hilarious.

Many knew Greg as “the guy from the roasts.” The shows enhanced his notoriety, but they may have detracted from his broader standup talents. To fervent fans, calling Greg a roast comedian is like calling Michael Jordan as a slam-dunk champion. Roasts were an exhibition where Greg excelled, but they did not encompass his overall comedic style.

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