Here’s a great, easy game you can play when bored: Think of the most absurd pairings of Saturday Night Live host and musical guest possible. Everyone in the room affects their best Don Pardo impression and says something like “Muuusical guuuest: Biz Markie…and starrrrring: Max Headroom.”
But here’s the thing. These wacky combinations exist. In the 37 years since SNL has been on, there have been some outrageous pairings. Some you’ll remember, some you’ve forgotten, and some came before your time. This doesn’t mean they were *bad* pairings — in fact, the eclectic mixes make for fun shows when people come from different worlds. Still, they’re noteworthy in some way. So after a careful examination of the full archives, we’ve determined these are the 30 oddest pairings in history.
Of course, feel free to use Don Pardo’s voice in your head as you read these.
Steve Forbes & Rage Against the Machine — April 13, 1996
Because nothing says rage against the machine quite like this billionaire peddling flat tax jokes.
RATM, it should be noted, played only one song as a result of being kicked out of the building after the first of their two slots. In protest of Forbes’ hosting, the band unfurled two upside-down flags (distress!) from their amps during “Bulls On Parade,” something they were warned against. It’s a great story.
George Foreman & Hole — December 17, 1994
About the only thing these two have in common is that the former heavyweight champ named every single one of his five sons “George Foreman” and Courtney Love is a fucking mess.
Jackie Chan & Kid Rock — May 20, 2000
Kid Rock’s hit “Bawitdaba” was inspired by a conversation backstage in which Chan needed help finding an intern who had a prop for his next sketch, telling Rock he was looking for “Boy with the ball.”
Ed Koch & Dexy’s Midnight Runners — May 14, 1983
Al Gore & Phish — December 14, 2002
Fun coincidence: The former vice president made his first big splash since losing the general election held on November 7, 2000. The popular rock band Phish made its first public appearance together as a band since its last pre-hiatus show on October 7, 2000. It’s also possible that Al Gore’s son’s 2007 arrest for marijuana possession can be tied to meeting Vermont’s finest at SNL. (Too easy.)
Rudy Giuliani & Sarah McLachlan — November 22, 1997
She wants all the animals of the world to find good homes. He had the NYPD round up and kill NYC’s entire homeless population in the 1990s. That must’ve been a fun meeting.
Sally Field & Tony! Toni! Toné! — December 11, 1993
Nobody defined early ’90s R&B — the outfits, the DJ scratching, the soul synth, the dancing — quite like … Sally Field. It’s unknown whether the original title to TTT’s biggest hit was “Fields Good.”
Bonus fact: The amazingly talented Raphael Saadiq is the guy singing lead vocals in this band.
John McCain & the White Stripes — October 19, 2002
Jack and Meg White know a thing or to about lying (hey, you’re not bro & sis!), but it would’ve been way cooler if SNL managed to reunite War for this one and had McCain stuffed in a cage on stage.
Danny Aiello & Coolio — February 10, 1996
Up until this meeting, the Italian-American actor had been spending most his life living in the Gangsta’s Paradise without even realizing. Credit Coolio for the acknowledgment.
Sean Hayes & Shaggy — February 17, 2001
Nobody bangs girls on the bathroom floor like Jack from Will & Grace. They call him Mr. Bombastic.
Jeremy Irons & Fishbone — March 23, 1991
When you think “disparate, all-black oddball crew” of ska punks, you obviously think of the stage and screen actor who received his classical training at the Bristol Old Vic Theatre School.
Tom Arnold & Tupac — February 17, 1996
It’s interesting that 16 years after this oddball pairing, the dead one has the far brighter career.
Wayne Gretzky & Fine Young Cannibals — May 13, 1989
It’s almost as if the SNL producers said, “Who can we get to be the musical guest for when ‘The Great One’ hosts, a band that really encapsulates what it means to be the best ever at doing something? Holy shit, I got it, let’s call those guys who sing ‘She Drives Me Crazy.’” Their schedule was free.
Bob Newhart & Des’ree — February 11, 1995
You gotta be Bob, you gotta be bold, ya gotta be…eh, I got nuthin’. This is just hilarious.
George Steinbrenner & Morris Day and The Time — October 20, 1990
Bruce Springsteen would have made the most sense. You know, a pair of Bosses. But instead we’re left wondering whether Big Stein did “the dance” backstage. C’mon, how awesome would it be to see George do the sweet moves you think about every time “Jungle Love” comes on (which is…often?):
We’re just getting warmed up. Click Page 2 below for 15 more gems. Find out who Joan Rivers passed the Dutchie to, how Fred Willard whipped it and who P-Funk got stoned with…
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