12 Hall of Shame Jokes from Celebs Who Tried to Be Funny

12 Ashton Kutcher

As with Musk, this entire list could have been Punk’d pranks that went completely off-the-rails, especially the one that resulted in Zach Braff punching a 12-year-old. However, we’re gonna go with an event that happened during the show’s pilot, when it was titled Harassment and it involved pranking regular people instead of celebrities. 

A couple booked a hotel room for a Las Vegas vacation, and upon entering it, they discovered a fake dead body covered in fake blood, and two actors posing as security guards preventing them from leaving. Being let in on the prank did very little to calm the couple down, as they went on to sue Kutcher, MTV and the hotel for $10 million.

11 Ellen DeGeneres

On DeGeneres’ first show back after reports of her being responsible for a toxic workplace environment, she decided to make light of the issue in the most tone-deaf manner possible: “Let me give you some advice if anybody’s thinking of changing their title or giving yourself a nickname, do not go with the ‘be kind’ lady.”

10 Oliver Stone

In 2006, the Oscar-winning director cracked this joke at an awards show in England at a time when one of the biggest stories was the unsolved murders of five sex workers: “It’s great to be back in England. I feel like the Jack the Ripper days are back. Nothing ever changes here.”

9 Jimmy Kimmel

At this year’s Emmy Awards, Kimmel and Will Arnett did a bit about how Kimmel was too drunk to give out the next award on account of his show losing earlier, with Kimmel playing dead and Arnett dragging him on stage by his feet. Kimmel took it too far by remaining on the floor during Quinta Brunson’s acceptance speech for Outstanding Writing in a Comedy Series, and the late-night host faced heavy backlash for taking away from her moment. 

Kimmel had Brunson on his show the next night to clear the air, and to settle the score, she interrupted his monologue to finish her acceptance speech, but the damage had already been done.

8 Elon Musk

Musk has always tried so hard to get people to think he’s funny, and it’s only gotten worse since he took over Twitter. He’s had so many lousy attempts at comedy, but walking into Twitter HQ on day one of owning the company holding a bathroom sink saying, “Let that sink in,” was a new height of desperation. Half of the Twitter workforce was fired by the end of that day, the stock prices of all of his companies are in free fall and Twitter is now a cesspool of sociopaths. But cool pun, bruh!

7 Dane Cook

Tragedy plus time equals comedy, as the old saying goes. Only Cook obviously didn’t get the memo on the time part, as this is what he had to say six days after 12 people had died and 58 others were wounded by gunfire in a mass shooting during an opening night screening of The Dark Knight Rises: “If none of that would have happened, I’m pretty sure that somebody in that theater, about 25 minutes in, realizing it was a piece of crap, was probably like, ‘Ugh, fucking shoot me.’”

6 Ted Cruz

Cruz has had so many attempts at being funny blow up in his face over the years that it borders on a humiliation fetish. But he royally messed up back in 2021 when he decided to mock comedian Patton Oswalt for canceling two of his shows for the venues’ lack of coronavirus precautions by quote tweeting, “Both of his fans were disappointed.” 

Oswalt’s responses didn’t disappoint:

• “(sigh) Okay Ted, here we go… Not as disappointed as Texas was when you cut your Cancun vacation short and came home.” 
• “Ted, you tweeted this at 1 a.m. Put the phone down and return to liquid form for a few hours.” 
• “Ted, my fans are all at home, waiting to see you at the January 6th hearings.” 
• “I’m so flattered you took time from your porn scrolling for this, Ted.” 
• “Well, that was fun. As always Ted, you’re a friendless, cowardly embarrassment and your beard looks stupid.” 

5 Don West

George Zimmerman’s defense attorney, attempting a bit of humor during his opening arguments: “Knock-knock. Who’s there? George Zimmerman. George Zimmerman who? Ah, good. You’re on the jury.” 

Disregarding the fact that a murder trial is the last place you should be doing a stand-up routine, not to mention the lameness of playing both parts of a knock-knock joke — he and Zimmerman ultimately “won” that case because Florida.

4 Jeff Ross

Generally, any joke at a roast is fair game, but Ross mocking the death of fellow roaster Ludacris’ friend and Fast & Furious co-star Paul Walker was a step too far: “‘Move, bitch, get out of the way!’ is what Paul Walker should’ve told that tree.”

3 Chelsea Handler

When the Huffington Post had Handler live-tweet the Oscars for them, it did not go well. Handler congratulated Kenyan-born actress Lupita Nyong’o’s Best Supporting Actress win, then took the opportunity to plug her own comedy book Uganda Be Kidding Me on Amazon. Kenya, Uganda, same thing, right? She plugged the book again even more tastelessly with Best Picture winner 12 Years a Slave, tweeting, “Congratulations #12yearsaslave Go to Africa or buy #ugandabekiddingme.”

2 Adrien Brody

Let’s not forget the time that Brody hosted Saturday Night Live, and decided to don fake dreadlocks and adopt a fake Jamaican accent before introducing Jamaican rapper Sean Paul as the musical guest.

1 Dennis Miller

From the “What I Should’ve Said Was Nothing” Department: The morning after Michelle Wolf’s polarizing performance at the White House Correspondents’ Dinner, Miller bizarrely tweeted teasing a verbal nuking of Wolf, but wound up getting himself roasted to a crisp for stating he needed three days to do so. Miller soon deleted the tweet — which, for the record, read, “What a horrid human being Michelle Wolf is. I’m going to read up on her over the next couple of days and I will have a few brutally mean jokes about her by Wednesday” — and those jokes he promised never came to fruition.