Saying the words "Friar's Club" without scaring away millennials who only speak in memes. Making the celeb in the chair feel honored, but just humbled enough to not jump out a window. Showcasing TV-friendly material that has enough foul language to make Quentin Tarantino blush: The comedic roast walks a whole lot of fine lines -- it's just part of the delicate mix of sick burns, underhanded compliments, and unthinkable vocabulary that makes up the cocktail. But sometimes when you shake that cocktail, it explodes right in your face. Pause to remember five roasts that did just that, and had viewers wincing between the laughs all the way.
Justin Bieber: Too Fast, Too Furious, Too Soon
The 2015 Comedy Central roast of Justin Bieber should've been a momentous occasion -- yeah, it's weird that the Biebs got roasted in the first place, but at least we can all laugh at the teen pop star turned way-too-smug 20-something.
Unfortunately, everyone from Jeff Ross to Pete Davidson cast a cloud over the evening with jokes about the then-recent death of "The Fast and the Furious" series star Paul Walker. The tragic running theme was in such poor taste that even Ludacris complained, and when you've offended the man who wrote heartfelt ballads like "Hoes in My Room" and "Move Bitch," you know you've crossed a line.
Roseanne Flips the Script
Comedy Central's 2012 roast of Roseanne Barr is pretty middle-of-the-road -- you could say that Roseanne jokes are the gift that keeps on giving, but they were never really a gift in the first place. As her roasters waded through all the expected fat jokes, Roseanne turned the tables and put her infamous ex, Tom Arnold, right in the sniper sights. The result is something that felt way too personal for comfort, full of poison-tipped quips like, "I'm glad you have a good wife, Tom; I'm glad she isn't with you just for your money -- I mean, my money."
Ouch. Smells like someone burned the roast.
Lisa Lampanelli Hassles the Hoff
Gilbert Gottfried stood right on the "too far" line at the 2010 Comedy Central roast of David Hasselhoff, but Lisa Lampanelli sprinted on over it. At the time, the Hoff was vulnerable -- fresh off a tabloid streak when a video of him eating a hamburger while his kids implored him to stop drinking made the online rounds. The whole thing made the night feel a little pathetic, but Lisa took no prisoners. "The Queen of Mean" earned her title as she somehow managed to fit jabs about the Deepwater Horizon oil spill, race, Haiti, Roger Ebert's fatal cancer, and the Holocaust into less than five minutes of stage time. That's got to be some sort of record that should've never been set.
Chevy Chase Gets Weird
Being mean is a natural part of the roast's recipe. But something about the New York Friar's Club roast of Chevy Chase in 2002 just came off as sad and awkward. When the majority of his "Saturday Night Live" posse didn't show up, Chase sat through the whole torpid affair behind a pair of shades and an uncomfortably humorless scowl, somehow managing to make the audience feel like he was both a terrible sport and yet undeserving of the onslaught that came his way. This one just amped up the mean factor on far too many levels.
James Franco Plays Softball
In 2013, James Franco invited a bunch of his Judd Apatow-alumni buds to a fancy dinner, and they lightly ribbed him in what felt like an extended press junket rather than an envelope-pushing night of comedy. This Comedy Central-aired "roast," to use the term loosely, went way too far in the other direction -- it was a too-nice, undercooked dish with no bite and some very unfunny bark.
Just let Sarah Silverman leave this right here for you: "I can't tell if this is a dais or the line to suck Judd Apatow's balls."
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