The best Comedy Central Roast moments ever (and a few of the worst)

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The first Comedy Central roast was just a Friar’s Club event adapted for television. After that 1998 broadcast, the network did four more — one every year. Then, somebody got the bright idea that they could just keep doing them. And they have.

But starting in 2003, it was now called the Comedy Central Roast. With an average of a couple a year since then, we’ve gotten some really memorable burns. And we’ve also determined which celebrities are painfully unfunny. Either way, we’re more than happy to laugh at all of them again.

Why is the Comedy Central Roast so popular?

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Washed up celebrities are our favorite things to see being roasted, except for a few weeks around Christmas. [Public Domain Pictures, Linnaea Mallette]

Few shows on the network — or any network — get as much attention. There are a few reasons for that. And if you love watching, you probably have your own. But here’s what makes us tune in whenever a new one airs.

  • It’s unpredictable. The stuff they put on TV is wild enough. But when you start to hear about the jokes that were cut, you realize how crazy these shows are.
  • It’s sufficiently rare. We know Comedy Central has tried to cash in on the success of roasts. But we’ll never be as interested in a weekly show as the rare treat of a full roast.
  • It’s a trip down memory lane. Let’s be honest, A-list stars aren’t really lining up to be roasted. So we get to watch has-been actors and entertainers get brutalized. Then they turn the table on their washed-up friends. Fun!

Our favorite Comedy Central Roast moments

Even the worst roasts had some seriously funny moments. And even the best had their low points. So we’re going to try to rate some of our favorite moments regardless of context. We’re sure we’ll miss a bunch of them, so be sure to gripe about it in the comments below!

1. Jeff Ross on Drew Carey

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We’re starting with the first one. And that’s where the world was introduced to Jeff Ross’ roast expertise. The Friar’s Club favorite took on Drew Carey in 1998. The rest is Comedy Central Roast history.

Our favorite burn: “We all know Drew isn’t two-faced, or else why would he wear that one? It’s like Buddy Holly and Barney Rubble had a baby and then peed on it.”

2. Anthony Jeselnik on Donald Trump

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Back in 2011, we were blissfully unaware that the billionaire blowhard would become president. And we still had no idea just how funny Anthony Jeselnik was. Well, at least we were happy to find out about the latter. He’s gone on to deliver some riotously funny stand up comedy specials. But a lot of fans (like us) first discovered his material here.

Our favorite burn: “Every time Donald Trump gets his hair cut he gets it cut the exact same way: by accident.”

3. Norm MacDonald on Bob Saget

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Leave it to Norm to turn the Comedy Central Roast on its ear. While everybody else was going as raunchy as possible, he got laughs on the other extreme. Some of his jokes (most of them) were objectively terrible — on purpose. But he delivered them with such confidence we couldn’t help but laugh. More proof of our theory: Norm MacDonald is the best.

Our favorite burn: “Bob has a beautiful face, like a flower. Yeah, cauliflower.”

And then there were some duds

As if “The Situation” didn’t have a bad enough public image, he bombed spectacularly. And then there was the train wreck that was Ann Coulter’s effort to roast Rob Lowe. But the truth is, there are plenty of funny points in every Comedy Central Roast. Besides, you should probably kind of root for a few flops. That’s when the expert roasters can step in and say the things you wish you’d thought of.

RELATED: The funniest stand-up comedians of the past 100 years (kind of)

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