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James Christian Kimmel is an American television host and comedian, best known for hosting and producing Jimmy Kimmel Live!. Before late-night, Kimmel co-hosted Comedy Central’s The Man Show and Win Ben Stein's Money, and produced shows including Crank Yankers and The Andy Milonakis Show.
Over more than two decades, the show has delivered unforgettable moments filled with surprise and celebrity antics. Unexpected guest appearances, playful pranks, and memorable interviews have made the program a staple of late-night television.
Here is a list of the 10 iconic moments from Jimmy Kimmel Live!
Disclaimer: The following list is ranked in no particular order, and the opinions expressed belong solely to the author.
10 iconic moments from Jimmy Kimmel Live!
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1) Jimmy Kimmel and Matt Damon’s ongoing comic rivalry
One of the most recognizable running gags in late-night television is the playful feud between Jimmy Kimmel and actor Matt Damon. Since the early days of Jimmy Kimmel Live!, the two have carried on a mock rivalry that has become a signature element of the program.
While the dispute is entirely staged, it has produced comedic moments over the years.A standout came in 2013, when Damon staged a takeover of the show by tying up Kimmel and assuming the role of host for the night, creating one of the series’ most iconic episodes.
2) Rihanna stages April Fool’s prank on Kimmel
Rihanna once delivered one of late-night television’s most iconic pranks. In 2015, as part of an April Fool’s Day surprise, the global popstar teamed up with Jimmy Kimmel’s wife, Molly, to stage an unexpected wake-up call.
In the middle of the night, Rihanna and her crew entered the Kimmel household and performed her then-new single Bitch Better Have My Money directly in the comedian’s bedroom.
Though caught completely off guard, Kimmel responded with good humor, making the stunt an instant highlight in the long history of celebrity late-night antics.
3) President Obama reads ‘Mean Tweets’ on Jimmy Kimmel Live!
“Mean Tweets” has become a recognizable recurring segment on Jimmy Kimmel Live!, inviting public figures to read social media posts about themselves on camera.
The format offers humor and relatability, showing a different side of prominent personalities. Former President Barack Obama has participated in the segment on two occasions. His appearances showed his ability to engage with popular culture while connecting with audiences in an approachable way.
4) Kimmel honors Bob Saget with on-air tribute
The death of actor and comedian Bob Saget in January 2022 prompted tributes from across the entertainment industry. Among them, Jimmy Kimmel’s on-air remembrance stood out for its sincerity.
In a heartfelt segment on Jimmy Kimmel Live!, the host spoke about his close friendship with Saget, sharing personal stories that showcased the comedian’s kindness and influence on those around him. The tribute gave viewers a glimpse into their bond and emphasized the loss felt throughout the comedy community.
5) Jimmy Kimmel faces unexpected celebrity interruptions on live broadcast
In 2019, an audience on Jimmy Kimmel Live! witnessed an unexpected series of events firsthand. During a segment, actors Margot Robbie, Brad Pitt, and Leonardo DiCaprio made surprise appearances on stage while Kimmel was addressing viewers.
The unexpected interruptions left both the host and audience visibly surprised. DiCaprio added to the excitement by inviting the entire studio audience to the nearby premiere of Once Upon a Time in Hollywood, creating a spontaneous moment that captured the energy of live late-night television.
6) Kimmel’s Canada statehood prank
A recurring feature on Jimmy Kimmel Live! known as “Lie Witness News” has gained attention for exposing how people respond to fabricated headlines.
In one segment, the show’s crew asked passersby for their thoughts on the fictitious announcement that Canada was becoming the 51st state of the United States.
The responses, ranging from confident assertions to confused explanations, showcased the unpredictability of the segment. The episode reaffirmed the popularity of Kimmel’s street-interview format, where unscripted reactions often create the most entertaining moments.
7) Kimmel calls for gun reform in address following Uvalde School shooting
In May 2022, the United States was shaken by the mass shooting at Robb Elementary School in Uvalde, Texas, where 19 children and two adults were killed.
Kimmel, who has frequently used his late-night platform to respond to moments of national grief, opened Jimmy Kimmel Live! with a direct and solemn monologue.
Speaking without an audience present, he conveyed his sorrow over the tragedy and voiced frustration at the country’s ongoing failure to enact meaningful gun legislation. Kimmel urged viewers to contact lawmakers and demand reform, framing the issue as a matter of public responsibility rather than partisan debate.
His remarks showed the increasingly visible role late-night television plays in discussions around social and political crises, as entertainers step beyond comedy to engage with urgent national issues.
8) Kimmel and John Krasinski share annual holiday prank tradition
Each holiday season, Jimmy Kimmel and actor John Krasinski engage in a playful series of pranks that have become a recurring feature on Jimmy Kimmel Live!.
Their friendly rivalry has included Krasinski decorating Kimmel’s office extensively for Christmas, while Kimmel retaliated by posting yard sale signs around town for Krasinski’s home and surprising him with eggnog during a guest appearance.
When Krasinski’s wife, Emily Blunt, joined the festivities, she contributed by filling Kimmel’s car with ornaments and gift-wrapping it.
9) Kimmel and Ellen DeGeneres engage in playful ‘Nice-Off’ on live show
During a 2019 appearance on Jimmy Kimmel Live!, Ellen DeGeneres participated in a contest of kindness with the host, jokingly referred to as a “nice-off.”
The segment featured the two exchanging humorous boasts about their generosity and good deeds. While Kimmel attempted to assert his own record of goodwill, DeGeneres ultimately took the playful victory, showcasing the comedic chemistry between the two late-night personalities.
10) Jimmy Kimmel’s annual Halloween candy prank on YouTube
Jimmy Kimmel has leveraged social media to engage audiences beyond his late-night show, with one of his most popular initiatives being the annual Halloween YouTube Challenge.
In this segment, parents record themselves telling their children that all of their Halloween candy has been eaten. The children’s reactions vary widely, from shocked screams and tears to reluctant acceptance, creating engaging moments.
From playful pranks to tributes, Jimmy Kimmel Live! has delivered a wide range of moments that entertain and connect with audiences.
