Jimmy Kimmel, a four-time Oscars host himself, couldn’t resist bringing some classic late-night rivalry humor into the mix when he reacted to Conan O’Brien’s widely praised performance as the 2025 Oscars host. With his signature blend of sharp wit and showbiz insider knowledge, Kimmel’s Monday night monologue on Jimmy Kimmel Live delivered laughs—and a dash of friendly shade.
As the torch passed from Kimmel to O’Brien this year, it was clear there was mutual admiration between the two comedic heavyweights. But that didn’t stop Kimmel from dusting off one of the most infamous feuds in television history for a perfectly-timed jab at Jay Leno. Let’s break down the joke, the history behind it, and Kimmel’s genuine support for O’Brien’s Oscars debut.
A Classic Conan Callback
For those too young to remember—or lucky enough to have forgotten—the Conan O’Brien and Jay Leno saga is one of late-night television’s juiciest dramas. Kimmel didn’t just reference it on Monday’s show; he leaned into it with the ease of a man who’s been waiting 15 years to deliver this punchline.
“Conan O’Brien did a great job as host of the Oscars,” Kimmel said, flashing his signature grin. “In fact, they said, I read today, Conan did such a good job, the Oscars announced that next year they’re giving it to Jay Leno to host.” It was a perfectly crafted callback to the 2009 Tonight Show debacle, where O’Brien’s dream gig was unceremoniously yanked away after NBC’s failed experiment with Leno in primetime.
The moment worked because Kimmel knows his audience. Longtime late-night fans still remember the messy public breakup between NBC and O’Brien, and Kimmel has never been shy about taking sides. By reviving the feud for one more laugh, Kimmel proved that the scars of late-night wars might fade—but they never fully disappear.
From Rivalry to Respect
Despite the playful jabs, Kimmel has been nothing but supportive of Conan O’Brien’s foray into Oscars hosting. When O’Brien was announced as the 2025 host back in October, Kimmel didn’t just approve—he celebrated. “I believe this to be an EXCELLENT choice,” Kimmel wrote on X (formerly Twitter), showing genuine excitement for his fellow funnyman.
The love didn’t stop there. During O’Brien’s guest appearance on Jimmy Kimmel Live, the red-haired comedy legend revealed that Kimmel was the first person to call and congratulate him after the Oscars gig became official. Kimmel even gave him some hosting tips, passing along the wisdom that comes with standing on that daunting Oscars stage four times.
Kimmel’s Oscar advice wasn’t just technical—it was personal. He understands the pressure, the scrutiny, and the unpredictable moments that come with live television’s biggest night. So while Kimmel may be retiring from Oscar duties (at least for now), it’s clear he was happy to see the role land in O’Brien’s capable hands.
A Joke with a Side of History
The brilliance of Kimmel’s Leno joke isn’t just that it’s funny—it’s that it’s rooted in real television history. Back in 2010, when the Tonight Show disaster reached its peak, Kimmel went all-in on defending Conan. In one particularly memorable episode, Kimmel appeared in full Jay Leno makeup and wig, mercilessly mocking the late-night icon for his role in O’Brien’s ouster.
That wasn’t just a comedic bit—it was Kimmel publicly choosing sides. And he never backed down from his stance. For Kimmel, the Conan-Leno drama wasn’t just network politics; it was a symbol of how the old guard in television could steamroll talent in pursuit of ratings. By keeping the joke alive in 2025, Kimmel is reminding audiences that even in Hollywood, elephants never forget.
As much as Kimmel’s Leno dig was a callback, it also served as a reminder of how far O’Brien has come. From losing The Tonight Show to hosting Hollywood’s biggest night, Conan’s journey has been both tumultuous and triumphant. Kimmel’s joke was the ultimate inside-baseball way to celebrate his friend’s success.
A night for Conan, with a Kimmel twist
In true Jimmy Kimmel fashion, Monday’s monologue was the perfect blend of heartfelt praise and razor-sharp humor. While he cheered on Conan O’Brien for his standout Oscars debut, he couldn’t resist roasting the ghosts of late-night past. After all, what’s a little Hollywood back-patting without a punchline?
The Oscars may have been Conan’s night to shine, but Kimmel’s playful jab ensured that longtime comedy fans got a nostalgic reminder of one of late night’s messiest moments. And in the process, he proved that in the world of comedy, the best jokes are always worth revisiting—especially when they’re this good.