Top 5 Favorite Jimmy Kimmel Sketches

Jimmy Kimmel

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Only one man in late-night television gives reigning viral video king Jimmy Fallon any kind of run for his money when it comes to sketch comedy. And that is the other Jimmy. Like his late-night counterpart, Jimmy Kimmel is known for crafting hilarious videos, sketches, and pranks—and he understands the power of social media and word of mouth. Because, really, that's the power Kimmel and Fallon harness day in and day out—creating moments they share online—which are then shared again and again and again on news feeds across Twitter and Facebook.

And Kimmel's work does what it's supposed to do. Make us laugh. Clever and fun, silly and topical—his sketches have all the hallmarks of what makes a late-night talk show different than any other genre on TV. So much so that it would be difficult to name an absolute favorite. But these five come close to the top. 

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I'm F*@#ing Ben Affleck

Back in 2008, when Kimmel was dating comedian and actress Sarah Silverman, she dropped a literal F-bomb on Kimmel with a musical number titled "I'm F*@#ing Matt Damon." The video aired on Kimmel's show and featured Damon singing along with Silverman as she recounted one of their trysts. 

Not to be outdone, Kimmel countered with his own video, titled "I'm F*@#ing Ben Affleck." Like Silverman's, the video featured actor and longtime Damon collaborator Ben Affleck singing alongside Kimmel and verifying their torrid affair. It also features a hilarious cameo by another big movie star. In many ways, these two videos demonstrated the full power of social media, as the video was shared thousands of times and viewed way more (over three million times and counting) on YouTube.

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Worst Twerking Fail Ever

In mid-summer 2013, a video titled "Worst Twerking Fail EVER" made the rounds in social media. You may have seen it posted on Facebook or heard it on some late-night entertainment program. In just a couple days, the video nabbed more than nine million views. Except, it wasn't the "Worst Twerking Fail" AT ALL. It was a prank, perpetrated by Kimmel. In the video, a young woman does her best "twerk"—a dance move in which you shake your butt as fast as you can—but collapses when her friend comes in the door. She crashes through a table and accidentally catches her pants on fire.

In his reveal, Kimmel walks into the room after the accident in a classic "Gotcha" moment and puts the fire out. The woman in the video is actually a Hollywood stuntwoman. The most amazing thing is that Kimmel and his team uploaded it to YouTube without any fanfare. They didn't share it, Tweet it, mention it, or do anything extra to promote it. To date, it has over 1.7 million views.

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Academy Awards Movie Parodies

Kimmel seems to feature some of his best parodies during his Academy Award after shows. This one followed the 84th Annual Academy Awards in 2012. Titled "Movie: The Movie," Kimmel served up a hilarious brew of silliness, parodying the big movies and Oscar nominees of 2011. Kimmel's goal was to "make the biggest, most star-studded film in the history of American cinema." Kimmel crossed genres, blew the budget, and delivered a parody worthy of a sequel. The film features Taylor Lautner, Antonio Banderas, Ed Norton, Josh Brolin, Charlize Theron, Helen Miren, Meryl Streep (in a mustache), Chewbacca, and Tom Hanks (as RoboLawyer), among dozens of others. It mocks horror films, legal thrillers, the Air Bud franchise, and more.

Then he came back the next year and did it again with "Movie: The Movie 2V," with just as much hilarity and star-studdedness. Poking fun at "The Avengers" and the "Twilight" series, "Movie: The Movie 2V" includes Rachel Weisz, Topher Grace, and Jon Krasinski as "The Shrimp," a superhero sharing the same origin story as several different superheroes. Even Oprah Winfrey makes an appearance as The President of the United States.

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Handsome Men's Club

This post-Oscars sketch from 2010 shows Kimmel taking part in a regular meeting of the Handsome Men's Club. Fellow club members Patrick Dempsey, Sting, and Rob Lowe share meeting notes and updates. The sketch centers around whether or not to accept Tyler Lautner and Robert Pattinson as new club members. The members agree, but Kimmel overrules, calling the actors "cute," not handsome. In a memorable moment, Jon Krasinski asks, "What's wrong with cute?" Kimmel answers, "There's a quota. And you filled it." Trouble brews when member Matthew McConaughey moves to vote on a new president.

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Kimmel Pitches Oprah

Here, Kimmel pitches a slew of new shows for Oprah's television channel, OWN, including Oprah's Book Club Fight Club. The pitch is exactly as it sounds. Book club members solve disagreements by duking it out. Club members include Oprah, who plants a haymaker on a fellow reader and then flexes and roars like the Incredible Hulk.