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Guests In Celebrity Roasts That Misunderstood The Assignment And Unexpectedly Got Their Feelings Hurt

It’s time for a good sit-down and ego-bruising for these celebs.

Guests In Celebrity Roasts That Misunderstood The Assignment And Unexpectedly Got Their Feelings Hurt

Celebrity roasts are built on one simple promise, nobody gets to leave untouched. The jokes land fast, the crowd laughs harder, and the guest of honor is supposed to take it all in stride.

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That is easier said than done when the punchlines start hitting old friends, personal insecurities, and the kind of awkward history that does not stay funny for long. Some roasts turn into a master class in taking a joke, while others leave people visibly rattled.

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These moments show exactly how quickly a roast can go from playful to painfully personal. Read on.

1. Jonah Hill and Sarah Silverman Came at Each Other Even Though the Actual Guest Wasn’t Either of Them.

Sarah started to joke about Hill being lured onto the stage by using a blunt and then proceeded to throw jokes about his weight.

1. Jonah Hill and Sarah Silverman Came at Each Other Even Though the Actual Guest Wasn’t Either of Them. Screenshot from Youtube video/Comedy Central
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Of Course, Jonah Didn’t Let the Opportunity Pass and Focused on Silverman’s Romantic Aspects and Age.

Sarah admitted that although she’s been through the whole roast process many times, she was still unexpectedly hurt.

Of Course, Jonah Didn’t Let the Opportunity Pass and Focused on Silverman’s Romantic Aspects and Age. Screenshot from Youtube video/Comedy Central
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2. Rob Lowe Was the Guest of Comedy Honor One Time, and Somehow the Tables Turned to Ann Coulter.

Ann Coulter said that she was blindsided by the jokes directed at her instead and felt that they purposely created that evil edit using her clips.

2. Rob Lowe Was the Guest of Comedy Honor One Time, and Somehow the Tables Turned to Ann Coulter. Screenshot from Youtube video/New York Magazine

Natasha passed on the third invite after deciding she was not ready for the kind of jokes that would come her way so soon after having a baby.

This also feels like the sibling fight over splitting an extravagant family dinner bill, where “fair” turned into accusations fast.

4. Merciless Roasters Are Used to the Game, and Usually There’s No Insult That Would Break Their Wall, but One Time Nikki Glaser Got Hit.

4. Merciless Roasters Are Used to the Game, and Usually There’s No Insult That Would Break Their Wall, but One Time Nikki Glaser Got Hit. Screenshot from Youtube video/ 15SecShortFun

It Was an Insult About Her Appearance After Nikki Had Already Made Her Feelings Known for Him.

It Was an Insult About Her Appearance After Nikki Had Already Made Her Feelings Known for Him. Screenshot from Youtube video/15SecShortFun

5. The Late Bob Saget Would Often Take the Jokes Like a Good Sport as Long as the Subjects Weren’t the Olsen Twins.

In a 2008 roast, Jeff Ross threw a joke that involved Mary-Kate Olsen, and Saget didn’t take it lightly since he’s very protective of them.

5. The Late Bob Saget Would Often Take the Jokes Like a Good Sport as Long as the Subjects Weren’t the Olsen Twins. Screenshot from Youtube video/Gavin Faker Baker

6. Chevy Chase Was Supposed to Be the Main Event in a 2002 Roast, but What Hurt More Than the Jokes Were His Comedy Friends Who Didn’t Show Up for It.

6. Chevy Chase Was Supposed to Be the Main Event in a 2002 Roast, but What Hurt More Than the Jokes Were His Comedy Friends Who Didn’t Show Up for It.Warner Bros.

Some roasts sting more when the people in the room know exactly where to aim.

Even celebrities with thick skin can feel it when the jokes come from friends, not strangers.

Want more celebrity chaos? See when the biggest stars wanted the earth to swallow them whole in this roundup of Hollywood’s most humiliating moments.

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