100 Best Albums After a busy 1987—the year in which Madonna not only starred in the movie Who’s That Girl, but also launched a hit single and a massive tour of the same name—the singer took a breather in 1988. But in early 1989, she split from husband Sean Penn, whom she’d married just four years earlier. Their divorce was soon finalised, and the newly single Material Girl arrived at a personal crossroads—one that fueled her landmark fourth album, Like a Prayer. From the gospel ecstasy of its chart-topping title track—and its controversial accompanying video, which mixed religion, racism and interracial desire as only Madonna could—Like a Prayer is the work of a pop sensation who’s made it through tabloid hell and has come out of the experience reborn as a true-blue artist. And while there’s only an occasional reference to the Penn breakup on Like a Prayer—most notably on the dizzying synth-pop bop “Till Death Do Us Part”—the album finds Madonna making the personal stuff about her, and not her ex. That means digging into her family trauma on “Promise to Try”, a heartfelt reflection on her mother’s death, and “Oh Father”, which takes a tough yet tender look at her daddy issues (“Oh Father”, in which Madonna stretches into Beatles-esque baroque pop, is one of several tracks on the album she wrote and produced with collaborator Patrick Leonard). All that soul-baring also results in Like a Prayer being her most soulful set since her 1983 self-titled debut. “Keep It Together” gives a knowing nod to Sly & the Family Stone, while “Love Song” is a funky meeting of music royalty between the Queen of Pop and Prince. Then there’s the massive “Express Yourself”, the worldwide smash Madonna co-created with Stephen Bray, her former Breakfast Club bandmate. Anthemic, affirming and undeniably powerful, the song is nothing short of Madonna’s “Respect”.