Bert Kreischer is one of the world’s most successful touring comedians, a host of two hit podcasts, and the star of the upcoming feature film The Machine, about his college years palling around with the Russian mafia. But 25 years ago, he was a young comedian who very mistakenly thought Will Smith expected him to have sex with him and 12 friends.
Kreischer recently told the story on Dana Carvey and David Spade’s Fly on the Wall podcast, and before you say “I’m sure he was just kidding,” he has told the story before — though sometimes in the telling, he only thought he would have to have sex with 10 of Smith’s friends.
And to be clear: There is no evidence of any kind that Will Smith or his many friends had any sexual interest in Bert Kreischer.
The Bert Kreischer Will Smith Story
It happened like this. When Kreischer, now 49, was in college, Rolling Story wrote a story about Kreischer, who was in his seventh year at Florida State University, that described him as “the top partyer at the Number One Party School in the country.” (Kreischer believes the story was the inspiration for the 2002 National Lampoon movie Van Wilder, starring Ryan Reynolds, for which Kreischer received no money or credit.)
The article made Kreischer a mini celebrity, and led to an invitation to do standup for a local radio station in Florida. After a very successful first outing as a performer, he decided to move to New York — where he crossed paths with Will Smith.
“Six months in, Will Smith discovers me. I’m doing stand up six months. I’m working the door at the Boston Comedy Club,” Kreishcer said, referring to the Manhattan venue.
“Did he ever lay hands on you?” joked Carvey, referring to Smith’s infamous slap of Carvey and Spade’s friend and fellow Saturday Night Live alum Chris Rock.
No, said Kreischer — but he added that his dad suspected Smith did want to lay hands on him in another sense.
Also Read: Bill Murray ‘Hated’ Chris Farley and Adam Sandler, Rob Schneider Says
“I go to meet Will at the record studio or wherever,” where Smith was recording his album Willenium, which was released in 1999. “And he goes, you’re cool, man. We should go, we should hang out. And I was like, Yeah, thinking, call me and we’ll hang out one day. And he goes, ‘What are you doing tonight?’ And I’m like, ‘Nothing.’ And he goes, ‘Let’s go to the movies.””
After the meeting, where Kreischer also told Smith he was a big hip-hop fan, Kreischer got in his car and called his dad.
“And he goes, ‘How’d it go?’ I go, good, we’re going to the movies.’ And my dad’s like, ‘On a date?… Oh buddy. I think he wants to f— you.’”
“That’s jumping ahead,” noted Spade.
Kreischer explains that his dad then told him that many men in Hollywood are so exhausted by constant sex with women that “the only thing that really excites them is the look on a boy’s face when they turn them.”
“Good God,” said Spade.
“I go ‘Dad, that’s impossible,’” said Kreischer. “He goes, ‘What’s more likely? The fact that you are so talented that in six months of doing stand up, the biggest movie star in the world wants to do a sitcom with you? Or that he’s tired of p—- and he wants to f— you?’
“And I was like, ‘What do I wear?’”
Following his father’s advice, Kreischer said, he dressed as sloppily as possible, in overalls and a sweater. He met Will Smith at their designated meeting spot, a Planet Hollywood restaurant. Someone told him to go downstairs, and, Kreisher said, he assumed he would have to have sex with him too. Then he went to the downstairs screening room.
“Then there’s 10 Black dudes in this room waiting for me. I’m doing the math, I’m like, ‘I’m sure he’s bringing Jazzy Jeff. That’s 13 dudes I’m gonna fppp tonight. He shows up with Jazzy Jeff, I swear to God, I swear to God.”
They watched the movie. No sex occurred. At the end, he said, Smith asked him: “What did you think?”
“It was a good movie,” he said.
“No, about the room,” he quoted Smith as saying.
“I don’t know — what do you mean?”
“The people!” he said Smith asked.
“The Black dudes?”
“No!” Kreischer quoted Smith as saying. “You said you were a hip-hop fan! That’s Kool Moe Dee, that’s Biz Markie…”
It was only then, Kreischer said, that he realized he had watched the movie with a screening room full of hip-hop icons.
“He brought all these hip-hop guys for me to meet,” Kreischer said. “I was like, ‘I could have f—ed Biz Markie?”
Despite the misunderstanding, things worked out OK for Kreischer. In addition to pulling in more than $23 million in touring last year, according to Pollstar, he will star with Mark Hamill in The Machine, which is based on a part of his college career that wasn’t that focus of that Rolling Stone article: That time he befriended Russian mobsters as an exchange student. Here’s that story, as he explains it in his standup routine:
You can listen to the whole Fly on the Wall podcast interview with Bert Kreischer here.