Who: Emmy-winning Jimmy Kimmel Live! host and comedian Jimmy Kimmel, 54, and Emmy-winning comedian Sarah Silverman, 51.
How They Met: The comedians first met in an aptly comedic way, at the N.Y. Friars Club Roast of Hugh Hefner in 2001. Kimmel was hosting and Silverman was obligated to make a joke at his expense. Her blow of choice? Describing her future boyfriend as "fat" with "no charisma."
And so a friendship was born. Kimmel hired Silverman for his prank call series, Crank Yankers, and around season two they "started hanging out and watching movies together."
"We had known each other for a while, just watching movies and stuff, just being friends," Silverman told Esquire in 2007. "And then one night we were watching Broadway Danny Rose. Jimmy went in for the first kiss, and both of us — we were probably nose to nose for what seemed like forty minutes before either of us had the guts to just go ahead and kiss. But once we did, we started making out like crazy. It had been festering for a very long time."
After a while, Silverman suggested they move to the bedroom, and all ambiguity went right … down the hall.
"He follows me down the hall, probably twenty-five feet to my bedroom, and I go into my bedroom and I turn around, and he's standing in my doorway, completely naked like a bear," Silverman remembered. "Like a big wild bear! I was shocked! I mean, at what point had all his clothes come off? And I looked at him like — I don't know, I just was taken aback."
After they started dating, Silverman addressed the jab that started it all: calling Kimmel "fat."
"It's weird looking back at that. I didn't know him at all back then," she told Entertainment Weekly in 2003. "I can't believe I called him fat. Knowing him now it's funny, because he has such a thin personality."
Why We Loved Them: Despite Kimmel's lack of charisma, the two settled into what appeared to be a sweet and loving relationship.
When asked why she didn't often bring her love life into her work, Silverman told The New York Times, "It's too pleasant to mine for comedy. He tickles my back until I fall asleep and stuff."
And then there were the Scrabble nights …
"When we have a night alone, like a Saturday night with no kids, we'll go to this restaurant we really like and sit at the bar and play Scrabble on our phones," she told Slate. "We have two games going, so we can go back and forth. There's constant action." The dream, no?
When They Peaked: Ah, the roast never really ended. In 2008, Silverman came on Kimmel's show to deliver a belated 40th birthday gift — er, confession? She was "Fucking Matt Damon."
So, naturally, Kimmel had to curate a flashy musical affair of his own — enter: "Fucking Ben Affleck."
The Breakup: In July 2008, People reported that the longtime couple had broken up.
Just a few months later, the magazine reported that Kimmel and Silverman were back on and "taking it slow."
By the following March, it was over for good.
A year later, Silverman opened up about the breakup in Playboy.
"I think Jimmy and I had every intention of spending the rest of our lives with each other," she said. "I love love. It's my top priority. Jimmy will tell you. I'm a good girl."
"We were together for so long and tried our best to make it work," she went on. "I can think of him now and don't have that edgy feeling anymore. I just love him to pieces."
"Sometimes loving each other isn't enough," she continued. "You have to be responsible for your own happiness. You can't stay in a relationship because you're afraid of the unknown. But I will always love him. Sometimes I think maybe we'll die together in our old age or something."
This is truly a twosome whose post-breakup relationship overshadowed their romantic one. Kimmel and Silverman remained tight following their split, and nearly a decade later the talk show host even spoke during his ex's Hollywood Walk of Fame ceremony.
"Sarah and I dated for seven years. She mentioned me in her 300-page autobiography four times. I looked it up last night. She mentioned farting 13 times. It has always been her first love," Kimmel joked at the ceremony.
"Sarah [Silverman] and I, we're like brothers," Kimmel told GQ in 2017. "It doesn't make sense to me that people would erase a big part of their lives. It's not like we didn't spend every day together for many years. We did, and we have a lot of things in common and mutual friends. I'll see something in the news and think, Oh, my God. I have to tell Sarah about this."
But despite the seeming ease, Kimmel admitted that his friendship with Silverman didn't bloom overnight. "It definitely took some time to be comfortable enough to be friends again," he told Andy Cohen on Watch What Happens Live.
Where They Are Now:
Kimmel married writer Molly McNearney in 2013. They two children: Jane, 7, and Billy, 4.
The late-night host's titular ABC show is currently in its 20th season.
Silverman went on to date Michael Sheen for about three years, between 2014 and 2017. She was most recently linked to comedian Rory Albanese, whom she's been with since 2020.
Next up for Silverman is an appearance in Jennifer Lopez and Owen Wilson romantic comedy Marry Me, which opens in theaters Feb. 11.
#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.
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