Exactly 30 years ago, Madonna turned the music world upside down by releasing an album of show tunes called I’m Breathless. Doubling as one of three (!) soundtracks to Dick Tracy, the staggeringly ambitious collection is a mix of Stephen Sondheim originals and campy, pop pastiches courtesy of regular collaborators Patrick Leonard and Shep Pettibone. The emphasis is on vocals and atmosphere instead of floor-fillers. It could have been a career-derailing misstep, but fans were more than willing to go along for the ride.

The genius of I’m Breathless is its ability to find the middle ground between Broadway fare and top 40 pop. Madonna wasn’t trying to bend and twist into another genre, she simply dismantled it and took the bits and pieces that pleased her. Take “Hanky Panky.” The ode to light S&M, which ranks as one of the most unlikely hits of the ’90s, wouldn’t sound out of place in Cabaret. It also works, however, squeezed between “Express Yourself” and “Cherish” in a stadium tour. The same goes for the wonderfully demented “I’m Going Bananas.”

More traditional in their sound and aesthetic are the glorious Sondheim contributions. Madonna nails the Oscar-winning “Sooner Or Later,” showing range that surprised even her most ardent detractors. “More” sounds like the Broadway equivalent of “Material Girl,” while “What Can You Loose” is the duet with Mandy Patinkin you didn’t know you needed. If I had to pick a favorite cut, however, that honor would go to one of the non-Sondheim songs. “Something To Remember” still holds up as one of the Queen of Pop’s best ballads 30 years on.

Despite the genre flip, I’m Breathless was a massive hit around the world — selling seven million copies. Admittedly, a large proportion of those sales can be attributed to the addition of “Vogue.” While that bop sounds out of place on the album, it makes complete sense from a marketing perspective. Revisit I’m Breathless below.

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