17. Madonna, “Into the Groove” (1985)
With two hit albums, Like a Virgin rising in the charts, and one wild MTV wedding cake performance behind her, Madonna’s career was in a very sweet spot in 1985. So it’s no wonder the It Girl would make moves in Hollywood, starring in Susan Seidelman’s Desperately Seeking Susan. It’s there, in the closing credits of the movie, that a demo version of “Into the Groove” was not just heard, but also essentially released.
“Music can be such a revelation,” preaches Madonna on “Into the Groove”, yet again making the dance floor a place for physical and emotional freedom. Playing shy, she bounces between earnestly begging for company and aggressively making her partner dance right to win her affection. While songs like “Borderline” and “Dress You Up” were successful dance-pop tracks, nothing Madonna had put out was as club-appropriate as “Into the Groove”. Penned by Madonna and songwriter Steve Bray, “Into the Groove” was initially intended for producer Mark Kamins. But Madonna thought it would suit her new movie well, much to the chagrin of Kamins.
The fact that Madonna would give the song such an unconventional debut shows how strong her popularity was at the time and how big of a hit the song really is. With filming finishing right before Like a Virgin was out, Desperately Seeking Susan swiftly became a Madonna vehicle before its release. Ratings were lowered specifically to accommodate the star’s teen fanbase and lead Rosanna Arquette was seen as a supporting actress in Madge’s shadow. The unpolished demo didn’t even land on the film’s soundtrack and was only available as the B-side to “Angel” in the U.S., but it’s still regarded as one of Madonna’s best dance tracks. —Hazel Cills
50. Madonna, “Like a Prayer” (1989)
Madonna filed for divorce from Sean Penn two months before she released “Like a Prayer”, the title track to the 1989 album that would cement her as a serious songwriter and an unstoppable cultural force as she entered her thirties. In anticipation of her fourth album, Madonna would grace the covers of Interview, Rolling Stone, and Spin. Like a Prayer was her most visible album to date, and also her darkest.
“This is reality, and reality sucks,” Madonna said in her Interview cover story. She was describing her initial vision for the “Like a Prayer” video, which was apparently even more brutal than the one that scandalized the Vatican, but the statement undercuts the whole song, too. Written toward the end of an abusive marriage, “Like a Prayer” sees Madonna assume a pose of surrender. Its gospel triumph comes only from its embrace of absolute darkness—”everyone must stand alone,” she sings into the emptiness. Then she’s falling from the sky, calling to God, or really just any power that will listen. She’s singing from her own rock bottom, waiting for someone—anyone—to carry her back up to the top. —Sasha Geffen
106. Madonna, “Borderline” (1984)
Released in 1983, “Borderline” is one of the first laid bricks in the cathedral of Madonna’s mythology, four minutes of emotional helium that became her first Top 10 hit on the heels of an iconic music video. In the clip, Madonna closes the gap between the club kid she was and the glamorous star she’d become as she plays her two beaux—a Latino tough boy and a snobby British photographer—off each other. Ironically, while lyrics refer to the gnawing desolation one might feel while navigating a relationship in which they don’t have any power, Madonna has total control in the video. She makes the tough boy miss his shot at the pool table by simply standing in the doorway; she spray paints the photographer’s car, causing him to flip out. She takes the energy from the song—a bubblegum instrumental given weight by her legible vocal performance—and uses it to dispel all the lingering demons from that bad relationship. There’s so much charisma, it’s easy to see why this was the song that catapulted her toward being the biggest pop star in the world. —Jeremy Gordon