Pop

“I have a reservation! What do you mean it’s not in the computer?!” “Act of Contrition” boasts a killer payoff, arguably the best to conclude a Madonna album, as the Queen of Pop plays up to her diva reputation in front of the Pearly Gates. But while it’s always fun to hear Madge leaning into her dry sense of humor, there’s not much of a song here. With its slightly perplexing blend of distorted guitars (courtesy Prince, at least in part), warped tape loops and Catholic prayer recitals, “Act of Contrition” sounds more like an improvised jam session plucked from the vaults for an oddities collection than an epilogue to a pop masterpiece. Listen here.

Two years before a planned duet with Michael Jackson fell apart, Madonna did manage to make it into the studio with the only other artist on her ‘80s superstar level, the inimitable Prince. Unfortunately, “Love Song” failed to live up to its A-list billing. Things start promisingly with a seductive French come-on and the Purple One’s signature slinky guitar licks, but the pair sounds more coquettish than flirtatious on a sparse funk number that never really shifts into second gear. Listen here.

Although continuing Madonna’s late ‘80s penchant for the sounds of Latin music, “Spanish Eyes” is a different beast to her summery Hot 100-toppers “La Isla Bonita” and “Who’s That Girl.” It’s hard to imagine anyone dancing the samba to a mournful acoustic ballad which, thanks to lines like “How many lives will they have to take? How much heartache?”, has been interpreted as a lament to victims of everything from war and gang violence to the AIDS epidemic. The fact that Like a Prayer came equipped with a safe sex factsheet about the “equal opportunity disease” – just another instance of Madonna’s strong allyship – certainly adds weight to the latter. Listen here.

“Promise to Try” is one of several Madonna songs in which she addresses the devastation of losing her mother at a young age. However, in a clever yet heartbreaking twist, this orchestral ballad finds the grown-up superstar imploring her grief-stricken five-year-old self to keep her memory alive (“Little girl don’t you forget her face/Laughing away your tears/When she was the one who felt all the pain”). It’s Like a Prayer’s most nakedly raw example of Madge’s songwriting maturity and further proof that when it came to emoting, she could match any of her powerhouse peers. Listen here.

Families, eh? Can’t live with them, you can’t live without them. That’s the general ethos of this Sly and the Family Stone-esque funk number in which Madonna acknowledges the bonds, however strained they may be, with her father and seven siblings (“Because blood is thicker than any other circumstance”). “Keep It Together” might not boast Like a Prayer’s most profound sentiment. Nevertheless, it was a welcome foreshadowing of the clubbier sounds Madge would explore more keenly in its follow-up and beyond. The fact it reached the Hot 100’s top 10 (thanks to a house-flavored remix) without a video also confirmed she was still very much in the midst of her first imperial phase. Listen here.

A true outlier in Madonna’s vast back catalog, “Dear Jessie” sounds nothing like she had recorded before or since. As implied by the self-deprecating cover art which referenced her early “Minnie Mouse on helium” criticisms, it’s certainly her most childlike offering. Inspired by a visit to the studio from Leonard’s daughter Jessie, this U.K. top 10 hit takes listeners on a musical magic carpet ride filled with wondrous visions of pink elephants, leprechauns and mermaids. And the sense of playfulness extends to the tempo-shifting production which segues from quirky lullaby to Sgt. Pepper-esque psychedelia with aplomb. Listen here.

In 2009, Madonna told Rolling Stone that “Cherish” is one of the most “r-tarded” hit songs she’s ever written. Even ignoring the politically incorrect phrase, this is one example where she’s dead wrong. Sure, Like a Prayer’s third single is frothier and more frivolous than its predecessors. However, its simple love story, inspired by the greatest of them all (hence the classic couplet “Romeo and Juliet, they never felt this way I bet”), provides some much-needed light relief in-between all the personal strife. A striking Herb Ritts-directed video, in which Madge playfully frolicked in the sea, only added to its carefree appeal. Listen here.

On the surface, “Till Death Do Us Part” sounds like a full-blown party anthem. Yet accompanying its propulsive beats and chiming synths is a rather harrowing depiction of a marriage with little worthy of celebration. No doubt ex-husband Sean Penn’s ears were burning – she filed for divorce just two months before Like a Prayer’s release – as Madonna sings of being belittled, betrayed and bruised, with the sound of shattered glass and references to flying vases evoking an atmosphere of domestic strife. Although Madge sounds typically self-assured, the closing line (“She’s had enough, she says the end/But she’ll come back, she knows it then”) suggests the song’s title is sadly all-too-prophetic. Listen here.

Hailed by Leonard as his finest Madonna co-write, this dramatic ballad finds the ice queen displaying a rare side of vulnerability while dissecting her complex relationship with her disciplinarian father. You can almost hear her voice crack when touching on the abandonment issues she felt following her mother’s death. But far from a character assassination, Madge also acknowledges his brand of tough love might not have been entirely intentional (“Maybe someday/When I look back I’ll be able to say/You didn’t mean to be cruel/Somebody hurt you too”). Described as a spiritual sequel to “Live to Tell,” “Oh Father” remains one of her most emotionally powerful moments. Listen here.

“Come on, girls! Do you believe in love? ‘Cause I got something to say about it.” From its opening call-to-arms, “Express Yourself” is Madonna in full-on self-empowerment mode. Five years after cheekily declaring herself a Material Girl, the star switched it up to tell fans that a man’s emotional intelligence is more important than his bank balance. Accompanied by David Fincher’s uber-camp homage to Fritz Lang’s Metropolis – then reportedly the most expensive video of all time – “Express Yourself” would have been the piece-de-resistance for any other pop album of the era. But with Madge firing on all cylinders, it had to settle for “second best, baby.” Listen here.

The video for “Like a Prayer” was considered so blasphemous everyone from Pepsi to the Pope essentially denounced Madonna (Pepsi eventually embraced the historic partnership, albeit three decades later). Even without all the controversial imagery, Madge’s three-week No. 1 smash was still likely to upset middle America, its lyrics famously drawing parallels between religious and sexual ecstasy. Yet the title track has far more than shock value to offer, whether it’s the slow-building funk-pop production, the gloriously uplifting harmonies from Andraé Crouch’s gospel choir or Madonna’s most commanding vocal of her glittering career.

“Life is a mystery,” goes the near-a cappella opening line. Like a Prayer’s monumental success, however, is certainly not. Watch here.