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Burned: The Oral F***ing History of the Comedy Central Roast

It is as old as TV itself: Take a star, one who’s been around long enough to make friends and ene­mies; sit them in a throne; wheel in a podium and a wet bar; and remove gloves. You hit that resilient, beloved figure with hard truths, cold lies, and raw abuse. The star feels bruised and dizzy but somehow honored, and everyone walks away happy. By 2003 the old ritual was dead, but a decade on, Comedy Central’s improbable modernization of the roast is now both a reliable ratings juggernaut and the greatest comedic-talent-breaking platform since the Carson-era Tonight Show or Saturday Night Live.

Still, back in the mid 1990s the mention of a “celebrity roast” brought to mind either the annual New York Friars Club Roast (fiercely private and often filthy) or the Dean Martin Celebrity Roasts (shticky, corny black-tie affairs televised on NBC in the ’70s and early ’80s). In other words, roasts were not hip.

Gilbert Gottfried (roaster): I watched the Dean Martin roasts. Back then mentioning a nudist colony counted as a dirty joke. Just saying something like “sleeping in the nude” was like talking about the strangest, most perverted act.
Doug Herzog (former president of Comedy Central, now president of Viacom Entertainment Group): In 1995 I’d come over to Comedy Central from MTV, where there were events like the VMAs and Spring Break. I thought, We need a comedy event. A one-night-only kind of thing. I grew up watching the Dean Martin roasts, so that was at the back of my mind. And living in New York, I’d sometimes attend the Friars roasts. They were filthy. Unairable. We had to figure out a way to combine the two.
A deal was brokered between Comedy Central and the Friars to broadcast the latter’s annual roasts on the network. The partnership lasted a few years, skewering the likes of Drew Carey, Hugh Hefner, and Chevy Chase before Comedy Central decided to go out on its own with the inaugural Comedy Central Roast in 2003, featuring roastee Denis Leary.
Doug Herzog: Denis Leary is a gigantic fan of Dean Martin, and I think he wanted to re-create that Rat Pack vibe.
Denis Leary (roastee, producer): Once my career took off, I became friends with Dean, which was really weird. He reached out and said, “Come to my house for dinner.” Still to this day it’s the biggest deal to me, even though he called me a pussy for nursing a beer the entire night. Anyway, with the roasts we were gonna inject some new blood into it. The set. The music. Sort of rock’n’roll.
With Leary on board, the stars came out: Kiefer Sutherland, Elizabeth Hurley, Christopher Walken, Jon Stewart, Conan O’Brien. The dais also showcased comics from the Boston stand-up scene where Leary began: Lenny Clarke, Nick DiPaolo, and a young Dane Cook. Jeff Garlin served as Roastmaster. The Leary roast was raw in a way the others hadn’t been. 
Denis Leary: The harder they hit you, the more info about them you’ll break out. Comedians bust each other’s balls, and I come from that neighborhood, so busting balls is everything.  
Nick DiPaolo (roaster): What I found most awkward is that I’m ripping people whose careers were 40 times more successful than mine. But if you’re a decent comic a roast is easy. You don’t have to learn insults. It’s in your DNA.