What Is Matt Rife's Connection To Ashton Kutcher And Mila Kunis?

Matt Rife's name is starting to appear in headlines alongside the likes of married "That '70s Show" stars Mila Kunis and Ashton Kutcher. Years before his razor-sharp jawline and relentless roasting of his audience members made him one of the top comedians on TikTok and a star in his own right, he was already leaving an impression on celebrities. It just wasn't always a good one.

Back in 2015, Rife was a cast member of the MTV series "Wild 'N Out" when he decided to shoot his shot with Zendaya by gently touching her face and pleading for her to give him her digits during a game. Instead, she moved her mug out of his reach and made no effort to hide her distaste over the unwanted invasion of her space. The rejection was so brutal that Twitter users still bring it up and roast Rife over it to this day.

Rife did another female celebrity wrong in 2019. Two years prior, he'd raised his profile exponentially by dating Kate Beckinsale. TMZ asked him if he had any advice for Beckinsale's boyfriend at the time, Pete Davidson, and Rife likely made other female stars wary of him as a potential romantic partner when he dissed Beckinsale by saying that he would tell Davidson to bolt. Rife has also tried to shoot his shot with Kunis, but it was all in the name of comedy.

When Matt Rife launched his "ProbleMATTic World Tour," it didn't take much convincing to get Ashton Kutcher and Mila Kunis to agree to shoot a video promo for the hot-ticket event. He told "Access Hollywood" he was excited about working with the couple because he's a massive fan of "That '70s Show" and particularly fond of Kutcher's character Michael Kelso. "He has always been the character I've related to in all of TV history," said Rife of the perpetually dazed and confused himbo. Rife and Kunis happen to have the same talent agency, which is how he learned she is a fan. As it so happens, Kutcher is, too.

Rife spoke to Kutcher first about possibly appearing in a video promo for the "ProbleMATTic" tour. During their chat, he learned that Kutcher and Kunis cuddle up in bed and watch his stand-up. "Which is gross but flattering. Whatever gets you there," he quipped. Kunis later called Rife to speak to him herself. "She was just the absolute sweetest," said the comic.

Rife came up with the promo concept himself. He cast Kutcher as a genie who denies the comedian's wish to date Kunis, reminding him that she already has an awesome husband. A wish to replace Kutcher in the movie "Dude, Where's My Car?" is also shot down – but Kutcher finally agrees to grant his wish for a world tour. Kutcher's parting words to Rife are: "Don't get canceled."

Matt Rife got another celebrity endorsement from "Criminal Minds" star Shemar Moore. In one of his viral TikTok videos, Rife's crowd work skills are put to the ultimate test when the actor heckles him during one of his sets. At one point, Moore yells to him, "You ain't a n***a but act like one."

At the end of the show, Moore came up on stage and gave Rife a run for his money when it came to the volume of the excited screaming from the crowd. Moore informed the audience that his girlfriend, Jesiree Dizon, is one of Rife's many female fans. She's even willing to put her relationship at risk because she finds the comedian so attractive. "My girl comes to me, and she's like, 'Shemar, you're the sexiest motherf**ker in the world. You're the father of my daughter. But I want to f**k Matt Rife,'" Moore quipped. He also shared that he and Rife have a "bromance" now and revealed that what first impressed him about the comic is that he defied a stereotype. "This motherf***ker's funny, and he's pretty. But pretty people ain't supposed to be funny," he stated.

Speaking to "E! News," Rife said that his banter with Moore was one of the best interactions with an audience member he's ever had. "We've been boys ever since," he shared. "He's the coolest, nicest guy." Is that a buddy cop comedy we see in their future?