Team-ups between rock bands and rappers seem natural (even passé) in 2023, but back in 1986, rap and rock just did not mix. When Rick Rubin presented the idea of a rap-rock song to Aerosmith’s manager, he reportedly responded, “What’s rap?”

Despite some trepidation from both camps, the unlikely marriage between a washed-up rock band and an up-and-coming rap crew birthed “Walk this Way,” a track that became a monster crossover hit, introduced rap to every rock fan in the world, and completely saved Aerosmith’s career. It still slaps.

William Shatner took a lot of pop culture shit for the unintentionally hilarious “poetic readings” of pop songs he recorded back in the 1960s. He returned to the form in 1995 and permanently shut everyone up about it. With the help of indie darling Ben Folds and other heavy hitting guests, Captain Kirk put out Has Been, an album of spoken-word pop/rock that kills. Not ironically, not as a joke, but for real. Listen to the cover of Pulp’s “Common People” as evidence.

Alicia Keys is a classically-trained pianist and composer known for R&B and soul. Jack White is a self-taught guitarist known for primitivist rock. James Bond brought this odd couple together in 2008 to record the movie theme “Another Way to Die.” The difference in style highlights what’s awesome about each performer, particularly in the too-brief break where Keys mimics White’s dirty guitar lines with her beautiful voice.

The merger of experimental drug-rock pioneers The Flaming Lips with Miley “Party in the USA” Cyrus only makes sense on paper if it’s blotter paper, but their weirdo cover of The Beatles’ “Lucy in the Sky with Diamonds” sounds like it was made by artists who are fully on the same vibe (or the same substances). The collaboration between these from-different-worlds artists continued on Cyrus’s “Dooo it,” which is also awesome.

Norah Jones is best known for jazzy, adult-contemporary hits like “Come Away with Me,” and “Don’t Know Why.” Billie Joe Armstrong is best known as the singer of pop-punk monsters Green Day. So the existence of Foreverly, a collaborative collection of Everly Brothers covers, is a head-scratcher. That it actually works (depending on your tolerance for “roots” music) is even more unexpected.

John Lennon is often cast as the “cutting-edge” Beatle, with Paul McCartney seen as the safe, middle-of-the-road, pop-hook-making one. But this collaboration with Kanye and Rihanna shatters the myth and must have left Sr. Paul’s geriatric fanbase scratching their heads and asking, “What does it mean to be 4-5-seconds from wildin’?”

“It’s more a question of me feeling lucky that these people are interested [in working with me] and think that I can bring something to it. For me, I feel great. I like diversity,” McCartney said of the team-up. What a friendly guy.

Since I’m on weird Macca collabs, I can’t overlook 2000’s Liverpool Sound Collage: a bizarre experimental electronic album that teams McCartney, Super Furry Animals, and Killing Joke’s Youth. Nominated for 2001 Grammy for Best Alternative Music Album, Liverpool Sound Collage mashes up Beatles studio chatter, found sounds, and various synth drones and bloops into—whatever this is. It’s not easy to get into, but it’s definitely unique.

Eminem’s 2018 album Kamikaze is all about conflict—dude is mad at everybody here, and wants you to know all about it—so it’s fitting that polite indie folk singer Justin Vernon would pretty much disown his contribution to Em’s “Fall.” Vernon says that he was not in the studio when the track was recorded, and that he tried to get Eminem’s team to excise a homophobic slur on the song.

To a casual listener, The Mountain Goats (aka John Darnielle) and Aesop Rock live at opposite sides of the sonic universe—Darnielle traffics in guitar-driven singer-songwriter songs that you could call “folky,” and Aesop Rock is a rapper and producer known for hard beats and dense lyrics. But look deeper and you’ll find a pair of fellow travelers—experimental, uncompromising, perpetual-outsider artists following their respective voices wherever they lead. Maybe that’s why their collaborations sound so weird and work so well. I wish there was more than just the above track and this re-mix, though.

I love both David Bowie and Bing Crosby, but I have always disliked this treacly, drippy version of “The Little Drummer Boy.” I’m clearly in a tiny minority, though, as this tune has become a perennial holiday classic, pulled from mothballs every Christmas like a beloved tree-topper. It’s undeniably fascinating to listen to two absolute icons from different eras raise their voices together in a plea for peace, but did it have to be on the worst Christmas song ever written? Did they have to include those wack-ass violins? Whatever. I’m a crank. Enjoy.

You could include every track on 1993’s Judgement Night in a list of unlikely collaborations that somehow work. A soundtrack album that’s about a million times better than the movie it came from, Judgement Night teams Mudhoney with Sir Mix-a-Lot, Ice-T with Slayer, Dinosaur Jr. with Del the Funky Homosapien, and more. Weed-enjoying rappers Cypress Hill getting down with experimental, underground art-rockers Sonic Youth is probably the weirdest pairing, but their song is thrown together and obvious; De La Soul desperately lamenting their lost fame over Teenage Fanclub’s dreamy guitars is anything but. That opening line: “Hey yo, kids! Remember when I used to be dope?” is a classic.

Boy pop meets dad rock in this cover of Queen’s “We Will Rock You,” and the result is—well listen to it. Queen’s original hit is extremely cheesy bubblegum rock that sucks, but adding white boy raps from British blokes in place of Freddy Mercury’s vocals takes the cheese to legendary levels. It’s so 90s (even though it came out in 2000 and the song is from the 70s), and so catchy, and so stupid, and so gloriously shameless that you have to respect it. Begrudgingly.