Zach Galifianakis on his first encounters with...

Read our issue 46 feature on Zach Galifianakis here.

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...Sean Penn:
"He called my cell phone and was like, 'Hey, it's Sean Penn.' And I'm like, 'Uh-huh...' He's like, 'What are you doing next week?' And I said, 'I'm going to Arby's.' Then I kinda realized it was him. I didn't audition [for Into the Wild]; I just showed up to South Dakota. It was me and him and Vince Vaughn and Emile Hirsch in a hunting lodge together for two weeks. But when I first got there, I said to Sean, 'How do you know me?' and he said he'd seen Out Cold about 17 times. His son is a snowboarder, it's not like he's studying the works of Lee Majors."

...Fiona Apple:
"I first met Fiona at a club in Los Angeles called Largo. It's a place where musicians and comedians perform together. There would always be musicians hanging out at a comedy show and vice versa. I remember going up to Fiona and saying something like, 'I have diarrhea.' Something I didn't think someone like Fiona Apple would ever care to hear with that persona she has, I guess. She giggled at it, and we always had these weird sentences in exchange. I handed her this music video I'd done for this Anita Baker song ['You Bring Me Joy'], and we were kinda friendly. Then we made her video [for 'Not About Love']."

Watch Zach in Fiona Apple's video for "Not About Love" here. Zach's version of Anita Baker's "You Bring Me Joy": 


...Kanye West:
"I met Kanye through Largo as well, and he had also seen the Anita Baker video. He came to see me do stand-up, and that night he asked me to do a music video. I said, 'If you don't tell me what to do, I'll do it.' I think some people would be intimidated that it's Kanye West, but that shit doesn't impress me, that cockiness. It never has and it never will. The more cocky people are, if you act cocky back to them, they respect it. But he was quite nice about it. I just shot [the video for 'Can't Tell Me Nothing'] at my farm. Will Oldham happened to be visiting me, so we drank some whiskey and shot it. That was basically it."

Zach and Will Oldham' video for Kanye West's "Can't Tell Me Nothing":