Pete Davidson spending Halloween with Kim Kardashian might have rocked the internet, but it turns out the comedian has a history (good and bad) with the reality star and her famous family.
Two years before Kardashian filed for divorce from Kanye West, the Grammy winner made waves backstage at Saturday Night Live, wearing a “Make America Great Again” hat during the closing credits after he hosted an episode of the sketch comedy series in September 2018. Following his appearance on the season 44 premiere, audio of West ranting about politics and raving about then-President Donald Trump surfaced. Davidson subsequently called out the musician.

What Kanye said after we went off the air last week was one of the worst, most awkward things I’ve seen here, and I’ve seen Chevy Chase speak to an intern,” Davidson said on the “Weekend Update” segment. “Kanye is a genius, but a musical genius. Like Joey Chestnut is a hot dog-eating genius, but I don’t want to hear Joey Chestnut’s opinions about things that aren’t hot dog-related. … Kanye, I know you’re like, ‘This is the real me, I’m off the meds.’ Take ’em. There’s no shame in the medicine game. I’m on them. It’s great.”
Things between Davidson and West, who have both been candid about their mental health ups and downs, were fine by January 2019 when they both attended Kid Cudi’s birthday party alongside Kim and Timothée Chalamet.

I got there a little early so I could give them my card. I thought it was just, like, us three,” the Set It Up star told Jimmy Fallon about the Nobu outing. “Kanye goes, ‘Let’s get the special room in the back,’ and I was like, ‘Oh no.”
After West ordered “[food] that’s not even on the menu — that crazy stuff,” Davidson joked he texted his agent to “book more shows.”

It’s not like it’s Applebees. It’s Nobu, which is like 77 Applebees’s,” he concluded about picking up the expensive tab.
Fast-forward two years and Kardashian is the one hosting SNL. During her October 2021 appearance on the NBC series, she shared the stage with Davidson in several skits, including one in which she played sister Kourtney Kardashian and he channeled BFF Machine Gun Kelly. During an Aladdin-themed spoof, Kim and Davidson kissed.

Kanye and Kim were in touch throughout the week on her outfits for the show, the skits and opening monologue,” a source told Us Weekly regarding West’s feelings about his estranged spouse’s performance. “They are not together romantically anymore, but they are still work collaborators.”
Later that month, Kim stepped out with Davidson, Kourtney, the Poosh founder’s fiancé, Travis Barker, and more friends on Halloween. While they were spotted holding hands on a roller-coaster, a source told Us at the time that things were platonic between the KKW Beauty CEO and the actor.

After West made headlines for his pro-Trump rant backstage at SNL in September 2018, Davidson slammed him during a “Weekend Update” segment the following week.
“You know how wrong about politics you have to be for me to notice?” he said. “Being mentally ill is not an excuse to act like a jackass. I’m quoting my therapist, my mom, and my mailman.”
Davidson ended the bit by putting on a “Make Kanye 2006 Again” hat.

Two months after the SNL shade, Davidson praised West after his ex-fiancée, Ariana Grande, was accused of mocking the Yeezy designer’s feud with Drake.

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By US Magazine

Dear Pete you will be in Kanye’s shoes in about a year.

Source: @kanyewest

How long will Pete Davidson Last?

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