
Jimmy Kimmel Roasts Ben Affleck for 'Dropping a Grenade' on Him and His Nemesis Jay Leno

Ben Affleck created a rather awkward moment for Jimmy Kimmel and Jay Leno, who had a feud for several years.
April 24 2025, Published 4:39 p.m. ET
Jimmy Kimmel didn’t mince words when it came to putting Ben Affleck on blast for creating an awkward moment between him and his former nemesis Jay Leno.
During Jimmy Kimmel Live! on Wednesday, April 23, the late-night host welcomed the Accountant actor and immediately dug into him.
Jimmy Kimmel recalled the time Ben Affleck left him with Jay Leno on Christmas day.
“You have that look on your face that you sometimes have when I see you, where you’re like, ‘What is he gonna do? Is he gonna do something?’ I’m not going to do anything,” Kimmel claimed before bringing up a memory he had of Affleck. “It’s not going to be like when I came to your house for Christmas, and I walk in the door and then Jay Leno walks right in after me.”

Jimmy Kimmel said he and Jay Leno made 'small talk' when they were left alone with each other.
As Kimmel stated how he made the most of the testy encounter, saying he and Leno were “uncomfortably making small talk,” Affleck interrupted the host and alleged he didn’t know much about the rift between the comedians.
“Believe it or not, I didn’t follow the nuance of your gossip history,” the movie star shared. “I was like, ‘Well, this is painful and awkward. What’s weird? Is something weird here? Have you guys been insulting each other publicly for decades? Oh well, Merry Christmas.’”
“Both of you left pretty quick,” the dad-of-three pointed out.

Jimmy Kimmel previously told Larry King he thought Jay Leno's gig on 'The Tonight Show' was 'premeditated.'
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The late-night host joked, “You just dropped a grenade right on us and left the room,” then admitting that Affleck’s recollection of the moment was “almost exactly how it went.”
Kimmel’s disdain for his fellow comedian stemmed from when the latter replaced Conan O’Brien on The Tonight Show in 2010. Over the years, Kimmel made note of his dislike for Leno on many occasions.

Jay Leno felt 'sucker-punched' by Jimmy Kimmel after their 2010 interview together.
In a 2012 interview with Larry King, Kimmel explained the origin of their controversy. “I always felt weird about how Jay got that 11:30 spot. Of course, that was NBC’s decision, but the whole thing seemed premeditated to me,” he admitted.
Though the former Academy Awards host wasn’t a fan of Leno at the time, he appeared on his talk show in 2010. Kimmel later told David Letterman that Leno “asked me 10 questions about nothing.”
The car enthusiast admitted he felt “sucker-punched” by Kimmel’s claim.

Jimmy Kimmel and Jay Leno have mended their relationship after their feud ignited in 2010.
The two comedians have since mended their differences.
During a 2017 appearance on The Hollywood Reporter’s “Awards Chatter” podcast, Kimmel detailed how Leno supported him when his young son Billy Kimmel underwent open heart surgery days after he was born, stating, "After my son had his operation, he called me, and he was very nice."