The 7 Best Pranks George Clooney Has Pulled on His Famous Friends, Plus 1 He Pulled on the Press

George Clooney is one of the best Hollywood pranksters (Getty Images)
George Clooney is one of the best Hollywood pranksters (Getty Images)

It takes a special kind of man to be a movie star capture the heart of a brilliant woman convince a friend his cat is dying of constipation. But George Clooney is exactly that kind of man. Over the last two decades, the actor has made headlines not only for his performances, but also for his pranks. In honor of April Fools' Day, we've rounded up some of the best and brightest from the Clooney archives in hopes that they might inspire the next generation of prank legends. (Amal Alamuddin, we're looking at you!)

1. That time he made Richard Kind think his cat hadn't had a bowel movement in weeks.

This is some vintage Clooney. In 1993, fresh off his divorce from Talia Balsam, George temporarily moved in with old friend Richard Kind. It turns out the Spin City star kept his cat's litter box in the guest bathroom, which George (his guest) was using. Each day, George would empty the litter box but say nothing to Richard. Naturally, Richard began to worry that his feline was woefully constipated — and eventually took the cat to the vet. Clooney then left his own special "present" in the box instead. Oh, George!

Richard Kind/George Clooney (Getty Images/WireImage)
Richard Kind/George Clooney (Getty Images/WireImage)

2. That time he gave Richard Kind a hideous painting he found in the trash and passed it off as his own work.

Poor Richard just can't get a break. Just three years after the infamous kitty litter prank, George's longtime pal got nailed again. It all started when Clooney found an awful, gigantic painting in a random pile of trash, took it home, framed it, and signed it as his own. Then for months, he kept telling Richard he was taking art classes. On Richard's 40th birthday, George gifted his friend the painting, which Kind dutifully hung in his living room.

"Everyone else knew but him," George recalled. "So everyone would come over and compliment him about the painting." Clooney finally came clean when he revealed the ruse five years later on a talk show. (Five years later, people!)

3. That time he challenged Brad Pitt's manhood with a bumper sticker.

To be fair, Brad Pitt kind of brought this one on himself. While filming Ocean's Twelve in 2004, the future Mrs. Angelina Jolie sent out a memo to the Italian crew saying that Clooney wanted to be referred to as "Danny Ocean" and forbidding anyone from making eye contact with the star. In retaliation, Clooney slapped bumper stickers on Pitt's car. One read, "I'm gay and I vote." The second was perhaps even more poetic and announced, "Small penis on board." Everywhere Brad drove, people waved and cheered. (There's no word though on how long it took him to notice the decals.)

Brad Pitt and Clooney (WireImage)
Brad Pitt and Clooney (WireImage)

4. That time he pretended to host the Jolie-Pitt wedding in Lake Como, Italy. In February.

Ever the equal-opportunist, Clooney doesn't limit his pranks only to his famous friends. In 2005, the dashing actor threw a fake wedding (yes, it sounds like a movie plot, but it's not) for Brad Pitt and Angelina Jolie to trick the press. Perhaps members of the media should have been more suspicious, considering George had set the affair at his mansion in Lake Como — a summer destination — but in February. The crafty star even ordered a smattering of high-top tables and had them set up on his lawn for helicopters to see.

Clooney confessed on the Today show, recalling that for two full weeks there were "hundreds and hundreds of press people outside the house, including people from all the entertainment shows." He seemed to be pretty proud of that one.

5. That time he filled producer Jerry Weintraub's underwear with M&Ms.

Airline flights can be long and boring, unless you're George Clooney. While up in the air with Brad Pitt and Jerry Weintraub in 2007, George and Brad playfully challenged the producer to a vodka-drinking contest. The catch? Neither actor was actually drinking vodka. They both had water. After Weintraub predictably passed out, the stars filled his underwear with M&Ms. Carry on, Clooney. Carry on.

 6. That time he filled Bill Murray's suitcase with 11 pounds of gravel.

But George doesn't only prank people when he's a houseguest. He pranks his houseguests as well. After staying at Clooney's abode in 2013, legendary comedian Bill Murray was having a hard time carrying his bags. Only when he opened them did he discover that George had considerately packed them with 11 pounds of gravel in the bottom. It's far from George's most original prank, but it's still one for the history books because, well, it's Bill Murray!

Matt Damon and Clooney suited up in Monuments Men (FameFlynet)
Matt Damon and Clooney suited up in Monuments Men (FameFlynet)

7. That time he convinced Matt Damon he was gaining weight.

If there's one thing that both famous movie stars and everyday folk can relate to, it's the struggle to lose weight, which is why the prank George pulled on his Monuments Men co-star Matt Damon was particularly amazing. Knowing that Damon was trying to shed a few pounds, George had a tailor take in Matt's pants by the slightest amount, just an eighth of an inch, every single day. Naturally, Matt was baffled.

"This was a job where I would go back to New York, where I was living with my family, and I would come back [to film in Europe] for two weeks," Damon explained of the prank. "And then I'd go back to New York, and every time I came back my pants were tighter, and I was like, 'Ugh, this is weird. I've been going to the gym!'" We've all been there, Matt… unfortunately, for most of us, Clooney wasn't having our pants made smaller.

8. That time he sent Tina Fey and Amy Poehler a complaint letter "written by Matt Damon."

After Tina Fey and Amy Poehler took aim at the famous womanizer (turned married man!) at the 2014 Golden Globes, George sent the hosts a complaint letter penned by Matt Damon, telling them he was offended by their joke about him being a garbage man.

"Look, it sounds hypocritical because I laughed at the jokes about George and Leo, but you know, that’s sort of what people think about them. But when you called me a garbage man, it just seemed like low hanging fruit," "Matt" lamented. As the real Matt later revealed on Late Show With Letterman, he didn't know he was part of this prank until he received two giant fruit baskets from Tina and Amy along with an "apology." Here's what the ladies had to say for themselves:

"If your note is part of some George Clooney prank, as I very strongly suspect it is, you A-list amateurs are going to have to step it the f*** up. We are not some easily confused starlets here. We are grown-a**, professional comedians."

And that, dear friends, is how you take a famous Clooney prank and make it your own