Will Oldham has been recording hauntingly beautiful folk music under the moniker Bonnie ‘Prince’ Billy since 1998, but a quick glance at his rap sheet confirms that the Kentucky-born weirdo-beardo is as multifaceted as any artist comes. From his uncredited cameo in Harmony Korine’s Julien Donky Boy, to the black and white photography work on the cover of iconic post-rock noodlers Slint’s Spiderland, Will Oldham’s creative output is as diverse as his moustache is large.

A sense of humour doesn’t always surface on Bonnie ‘Prince’ Billy records, but across a large catalogue of film, television, and music video credits, Will Oldham has shown us that he’s one of the funniest and strangest figures in folk music. He’s releasing a collaborative tribute to the Everly Brothers via Drag City Records today, and honestly, we’ll take any excuse to revisit these five hilariously awesome tidbits from Will Oldham’s creative rucksack.

The alternate video for Kanye West’s “Can’t Tell Me Nothin'”

This alternate music video for Kanye West’s “Can’t Tell Me Nothin'” is probably one of the things I’d pick to save if the Internet caught on fire and I could only carry a handful of YouTube videos. This collaboration came about after a mutual friend showed Kanye some of Zach Galiafinakis’ YouTube videos. Yeezy came out to see one of Zach’s standup sets, commissioned the video from him afterwards, and Zach flew home to shoot the video at his family farm in North Carolina the next day. Bonnie ‘Prince’ Billy happened to be visiting Zach in North Carolina, so he got in on the pelvic thrustery, and the rest is YouTube history.

His appearance as a police interrogator in Trapped In The Closet

It’s a small cameo, but just the fact that Will Oldham’s gleaming, bald head makes an appearance in Trapped In The Closet is enough to convince me that he’s up for anything. It also adds another layer to the Bonnie ‘Prince’ Billy/R. Kelly connection, which we’ll explore shortly.

His appearance as Pastor Pigmeat on Wonder Showzen

Oldham is heavily featured as a character named Pastor Pigmeat in the “Horse Apples” episode of the cringe-comedy series Wonder Showzen, a bizarre, absurdist parody of Sesame Street. The “Horse Apples” episode is a live-action parody of Hee-Haw, or the Blue Collar Comedy Tour, featuring David Cross, Zach Galiafinakis, Jon Glaser, and more giving us a mind-meltingly annoying slice of Middle America.

His appearance as a gorilla trainer in Jackass 3D

It just so happens that BPB’s cameo as a gorilla trainer in Jackass 3D is even funnier when dubbed in Spanish.

His cover of R. Kelly’s “World’s Greatest”

The connection between R. Kelly and Will Oldham is deep and pure. The humour in his “World’s Greatest” cover is subtle, but you’ll find it if you pay close enough attention to notice that Oldham stays true to R. Kelly’s mispronunciation of “ask” in the pre-chorus: “If anybody axe you who I am.” It’s clearly a cover that was born out of love and admiration; Oldham proves himself to be a historian well-equipped in discussing the lore surrounding the R&B singer in an interview he conducted with Kells for Interview Magazine. Here’s a worthwhile excerpt:

“WILL OLDHAM: Do you watch 30 Rock?

R. KELLY: No. What’s that?

OLDHAM: It’s a television show, a comedy, that takes place in all of these hallways. It’s pretty funny. It’s, like, a good sitcom. It’s got Alec Baldwin. You know Alec Baldwin?

KELLY: Alec Baldwin? Yeah! Don’t he have a brother and they all kind of look alike?

OLDHAM: They’re, like, four brothers.

KELLY: Steve Baldwin…

OLDHAM: Yeah, exactly.”

Oh, and there’s one more thing that makes Bonnie ‘Prince’ Billy the funniest guy in folk music: DAT BEARD.