How a bizarre 1983 studio idea led to one of music’s strangest collabs between the Prince of Darkness and the Queen of Pop.

It sounds like something dreamed up in a Sunset Strip recording studio at 3 a.m. after a few rounds of coke and whiskey, but believe it or not, in 1983, Ozzy Osbourne and Madonna did actually appear on the same song!

The track was “Shake Your Head (Let’s Go to Bed)” an experimental electro-dance track from Was (Not Was), the Detroit-based band fronted by musician/producer Don Was. The plan? Put Ozzy on lead vocals and pair him with a then-unknown Madonna on the duet.

It wasn’t pop. It wasn’t metal. It was something  that you might hear the Sprockets from Saturday Night Live listening to in an underground techno club somewhere in Germany in 1987.

“Shake Your Head (Let’s Go to Bed)” was slated for Was (Not Was)’s 1983 album Born to Laugh at Tornadoes. But just as quickly as the collaboration came together, it fell apart—because Madonna didn’t stay unknown for long.

Her self-titled debut dropped in July 1983, and almost overnight she went from East Village club kid to global superstar. With that came more control, and a hard no on the use of her vocals now that she was developing her own signature style. Just like that, the Ozzy–Madonna duet was shelved.

Later, Was brought in actress Kim Basinger to re-record the part, and the original became the kind of story that sounds too weird to be true.

Except it was true.

Accidentally Reviving an Ozzy/Madonna Collab

Nearly a decade later, “Shake Your Head (Let’s Go to Bed)” came back from the dead.

In the early Ninties, the song got a second life when it was remixed into a club track by producer Steve “Silk” Hurley. And that’s when destinies collided—or maybe just got mislabeled.

Legend has it that somewhere in the process, Hurley accidentally used Madonna’s original 1983 demo vocals.

The result? A remix featuring both Ozzy and Madonna—a long-lost collaboration that quietly slipped out on vinyl in the U.K. in 1992, including on copies of the Now Dance 92 compilation.

The story has since been confirmed by Don Was and Ozzy’s son, Louis Osbourne, who discussed it on Jack Osbourne’s podcast.

Prince’s Powerhouse ‘Prayer’ Support

Of course, Madonna’s brush with rock royalty didn’t end with Ozzy—it just got a little more intentional a few years later, when she teamed up with another legend: Prince.

But even by his own mythic standards, one of Prince’s most fascinating contributions to music has remained largely under the radar.

Most fans know about his funky slow-groove duet with Madonna on “Love Song” from Madge’s 1989 pop masterpiece Like a Prayer. But Prince’s most fascinating contribution to that record is buried in plain sight—hiding in the first few seconds of the album.

In fact, it’s Prince you hear on that album before you even hear Madonna’s voice.

Listen closely to the opening seconds of “Like a Prayer.” That scorching, bluesy guitar riff that kicks the church doors open before Madonna stumbles in? That’s Prince. Uncredited and unmistakable.

It’s a brief moment, but it sets the tone for everything that follows in a song that would go on to top the charts in over 30 countries.

Sunset Strip Connection

The awesome ’80s and grungy ’90s may now be history, but Madonna’s connection to rock never really went away.

Her guitar-driven edge—especially in her live shows—was shaped by the spirit of the Sunset Strip, which is where her longtime guitarist Monte Pittman once worked–at Guitar Center Sunset–before he was tapped to provide guitar lessons for Madonna and her then-husband Guy Richie.

Pittman would go on to become a longtime member of Madonna’s touring band, helping inject a harder edge into her live shows—proof that even the Queen of Pop has always had one foot planted firmly in rock and roll.

Today, when he’s not circling the globe with Madonna, you might still catch Pittman back on the Sunset Strip, plugging in at the Whisky A Go-Go for “Ultimate Jam Night Hollywood.”