Madonna & Warren Beatty, "Now I'm Following You" (1990)
Yes, Madonna and Beatty were in a relationship and co-starred in the film Dick Tracy, which inspired the I'm Breathless soundtrack album. However, hearing Warren Beatty warble alongside his then-girlfriend is certainly a little jarring. The couple was not long for this world, but at least Beatty scored another iconic movie music moment eight years later, when his 1998 political satire Bulworth produced the smash hit "Ghetto Supastar (That Is What You Are)."
Madonna & Ozzy Osbourne (via Was (Not Was)), "Shake Your Head" (1992)
Okay, so this isn't technically a "collaboration" in the sense that Madge and Ozzy Osbourne were ever in the studio together, but go with us for a second: Madonna recorded vocals for Was (Not Was)' "Shake Your Head" before she was famous in the early 1980s, though when the song was released in 1983, it did not include her vocals.
Then, in 1992, Was (Not Was) sought permission from Madonna -- who by that point had become the biggest female pop star on the planet -- to use her vocals for a new remix and reissue of "Shake Your Head." Madonna declined. So, Was (Not Was) enlisted actress Kim Basinger to supply the female vocals on the new version, which was included on the act's compilation Hello Dad… I'm In Jail. That track, re-tooled into a thumping dance cut by famed DJ/producer/remixer Steve "Silk" Hurley, became a smash hit in the U.K., and reached No. 4 on the Official U.K. Singles Chart.
Wait, so how does Madonna factor back into the saga of "Shake Your Head?" As legend has it, some of her vocals were accidentally used in Hurley's Dub Mix of the song, also released in 1992. (It was later issued in the U.S. as the Alternative Remix.) A vocalist that sounds strikingly like Madonna sings lyrics like "and you can't put your finger on the truth" while Osbourne wails "shake your head."
So, at some point in late 1992, if you were in a dance club, you might have been grooving to the sounds of Madonna and Ozzy Osbourne together. How's THAT for surprising?
Madonna & Vanilla Ice, SEX book/"Erotica" music video (1992)
Vanilla Ice is best known for his smash single "Ice Ice Baby," but soon after that mainstream rap song exploded, Robert Van Winkle showed off a very different side of himself in Madonna's ultra-controversial erotic coffee table book, Sex. Madonna and her then-boyfriend Vanilla Ice are together in some of the book's steamiest shots, while celebrities like Isabella Rossellini, Big Daddy Kane and Naomi Campbell also appeared. Most of the Sex celebs, including Vanilla, are also in Madonna's NSFW video for "Erotica," although one can only spot Mr. Van Winkle from the back in the clip.
Madonna & Sofia Coppola, "Deeper and Deeper" music video (1992)
Yup, that's the Lost In Translation auteur hanging out with Madge in the virtuoso video for "Deeper and Deeper," another boundary-pushing clip from her Erotica era. Gay-porn director Chi Chi LaRue and actress (and longtime Madonna pal) Debi Mazar also pop up in the clip, which finds Madonna sans eyebrows and navigating a sordid nightclub scene. Seven years after co-starring in the clip, Coppola would make her directorial debut with her adaptation of The Virgin Suicides.
Madonna & Everlast, "Waiting (Remix)" (1993)
Released as the B-side to the Erotica single "Rain," the remix of "Waiting" featured Everlast one year after scoring huge success as the frontman of House of Pain with "Jump Around," and five years before he remade himself into a sad-rap icon with the alternative hit "What It's Like." Hearing Everlast in full-on "Jump Around" mode is deliriously fun years after the fact: "I can get freaky like a Friday/I know you're going my way/Naked on the highway!" Everlast interjects on the thumpy track.
Madonna & Björk, "Bedtime Story" (1994)
Björk was fresh off of her debut album, 1993's Debut, when she co-wrote "Bedtime Story," the sleek house jam for Madonna's Bedtime Stories album. Listening to the song 20 years after its release, it's startling how much one can hear the Icelandic art-pop star's influence on the track: the minimal synth melody and Madonna's vocal delivery make the track something of a distant cousin to Björk's masterful "Hyperballad," released one year later. "Bedtime Story" is one of the few instances in Björk's discography in which she contributed songwriting but stayed away from the microphone.
Madonna & Tupac Shakur, "I'd Rather Be Your Lover" demo (1994)
"I'd Rather Be Your Lover" appears on 1994's Bedtime Stories as a collaboration with Meshell Ndegeocello, but Tupac Shakur was, apparently, originally supposed to lay down a verse on the studio track. For reasons still unknown, Madge/'Pac link-up never made it onto an album, but a demo leaked long ago in which Tupac playfully accuses Madonna of "tryna get me all up in your satin sheets." Sorry, Meshell, but it's hard to listen to the released version after hearing this one.
Madonna & Deepak Chopra, "Bittersweet" (1998)
In 1998, noted spiritualist Deepak Chopra commissioned some of his famous friends to read the mystical love poems of 13th century Persian writer Rumi along with some backing music, for a compilation album titled Gift of Love: Deepak & Friends Present Music Inspired By the Love Poems of Rumi. One of those friends was Madonna, who chose to utter lines like "I saw myself as the source of existence/I was there in the beginning/And I was the Spirit of Love" in front of a smoky new age tune called "Bittersweet." Not essential Madonna work by any means, but hey, sometimes we all have to be "whirling and dancing like a spinning wheel," right?
Madonna & Austin Powers, "Beautiful Stranger" music video (1999)
It's not surprising that Madonna co-starred alongside Mike Myers as Austin Powers, a character who was absolutely inescapable in the late 90's, in the video for a song on the Austin Powers: The Spy Who Shagged Me soundtrack. Looking back, though, that part where Madge rubs her butt against Austin Powers' cheek is pretty surprising! The "Beautiful Stranger" video looks like it was dropped into a 90's time capsule immediately upon release, and remains gloriously dated.
Madonna & Lil Wayne, "Revolver" (2009)
In the late 2000s, at the height of Lil Wayne's Tha Carter III fame, the rapper was the most in-demand MC on the planet… and often took on any project tossed his way, to great radio success. "Revolver," from Madonna's most recent greatest hits compilation Celebration, compares her love to a loaded gun, and lets Weezy slither in during the back half to deliver some ham-fisted rhymes about shooting to kill. "Revolver" never became a hit, but stands as an unexpected collaboration between two of pop's most prolific artists.