Top 10 Memorable Jimmy Kimmel Moments

Jimmy is a known prankster, but what about when a celebrity decides to turn the tables on him? This happened April Fool’s Day 2015 when Rihanna, with the help of Kimmel’s wife and crew, snuck into the host’s bedroom while he was sleeping just after 1am. She wasn’t alone though; in fact, she brought her dancers, a boombox, various props and at least two videographers. The group woke Kimmel up with a performance of her then-new song 'Bitch Better Have My Money'. And of course, a still groggy Jimmy took the prank in the spirit it was intended: all in good fun.

When Jimmy Kimmel wants to do a survey, he turns to the most honest people out there: kids. His roving reporters on Hollywood Boulevard have asked adorable youngsters questions like “Do you know any naughty words?” and “What’s the worst thing you ever heard mommy say?” but also asked them to explain serious hot-button issues like same-sex marriage. While it’s always a cute segment to watch, it’s also quite interesting to get a fresh perspective and see the world through the eyes of these children.

John Krasinski is Jimmy’s neighbor and friend, and every holiday season they take part in a series of competitive pranks that make for great television comedy. Once, John filled Jimmy’s office with Christmas decorations, while Jimmy put up signs across town for a yard sale at John’s place before dropping egg nog on The Office star as he sat in the guest’s chair. When John’s wife Emily Blunt joined in the fun, the couple had Jimmy’s car filled with bobbles before gift-wrapping it. These two clearly take the famous Christmas lyric “You better watch out” literally.

It’s really nice to see Jimmy and Ellen throw down. When she’s a guest on Kimmel’s show, she really impressed everyone with her kindness. Everyone except Kimmel, who felt that his own kindness to his staff was being challenged. He confronted her and the pair had a rap-battle style nice-off, complete with a pleasantly bloodthirsty cheering crowd. While Jimmy landed a few blows of niceness, it was, of course, Ellen who prevailed and reminded the Live! Host why he shouldn’t mess with her.

Jimmy Kimmel Live! was long established by 2013, but what really put him on the map as a prankster was the time he sent a reporter down to Coachella to ask attendees what they thought of certain bands. Not only were these bands not playing Coachella, but also most didn’t even exist. With names like The Chelsea Clintons and The Obesity Epidemic, it’s hilariously surprising that no one figured out this was a joke – in fact, some even had strong opinions on the fake acts. The success of the segment, however, meant people were wise to the prank when Kimmel tried to pull it again three years later.

It’s got everything you could possibly want in a Hollywood blockbuster - and that’s the point. During his 2012 post-Oscars show, Kimmel aired a trailer for Movie: The Movie starring George Clooney, Charlize Theron, Tom Hanks and pretty much anyone else who happens to be famous, up to and including Bryan Cranston. Of course it’s not a real film, but it could be, if all the major studios poured all their money into one project. We’ll just have to settle for the trailer version and – of course – the obligatory sequel trailer that came out the next year.

While asking celebrities to read mean things people have tweeted about them is a rather simple premise, it’s one that has caught on. This has made it one of Jimmy Kimmel’s most popular recurring bits and created some great moments on the show. Oscar-winning A-List actors like Robert DeNiro, music stars and YouTube Creators have all used the platform to read the words of their harshest critics and laugh or, in some cases, snap back. President Barack Obama himself even read the words of anonymous Twitter critics... as well as those of one he knows all too well.

Jimmy Kimmel is not afraid of using the long con to pull off a really funny stunt. In 2013, he posted a video of a woman twerking and accidentally setting her pants on fire under the name Caitlin Heller to YouTube and waited. After a couple of months, the video went viral and news outlets reported on it. Jimmy even aired the video as something he had discovered and then invited Heller on the show via Skype interview…. only she was already in the studio and was actually a stuntwoman named Daphne Avalon. The video, as only a few had suspected, was a staged Kimmel stunt.

He’s not the only TV comedian to embrace social media as a way of interacting with fans and generating content, but Jimmy Kimmel’s YouTube game is top notch. The biggest proof of this is his annual YouTube Challenge where he gets parents to send him videos where they tell their kids that they ate all of their Halloween candy. The responses the kids give range from falling down screaming and crying to disappointed acceptance. While some may say it’s a little bit mean, it has also led to some very funny and very real moments.

Before we unveil our top pick, here are a few honorable mentions:
- Jennifer Lawrence Gets Her Revenge on Chris Pratt

- “Friends” Reunion

- Jimmy Kimmel Lie Detective

When Jimmy Kimmel closed his show by randomly apologizing to Matt Damon for bumping him, it was supposed to be a one-time joke. The Jason Bourne actor wasn't scheduled to appear and if he was, they certainly wouldn’t have bumped him. Then Kimmel did it again, and again, and again until Damon finally took notice. This kicked off an often-hilarious spat that’s lasted over a decade. We've seen Damon take over Kimmel's show, and Jimmy audition for Matt's movie roles unsuccessfully. The pair even ended up in couple’s therapy twice. It's a fake celebrity feud that shows no signs of stopping, and that's a good thing.