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Madonna’s Top 20 Songs

on August 16, 2017, 1:15pm

15. “Music”

Music (2000)

“Music makes the people come together.” Yeah, pop can be pretty literal, but it doesn’t get more basic than that. Yet here we are talking about what’s arguably one of her biggest hits to date. Produced by French DJ Mirwais Ahmadzaï, who she thought was “the shit,” the track is nothing more than a comeback anthem, something to turn heads, and given the critical and commercial success of Ray of Light, she really needed something epic to slam down. So, on August 21st, 2000, “Music” punched hard: on the charts, on the radio, all over MTV and VH1, and, most importantly, every club across the world. It’s almost meta come to think of it; the song did make people come together. Hey, Mr. DJ… –Michael Roffman

14. “Deeper and Deeper”

Erotica (1992)

Erotica‘s eccentric second single was an aural sigh of relief when held up to the exaggerated sexual album as a whole, regardless of its perverted lyrical metaphor (depending how you read into it). The fusion of flamenco guitars, chummy disco, and castanet percussion helped orchestrate a tale of a young man accepting his own homosexuality — a bold move given it was still a taboo subject in 1992. What’s even bolder was its nods to The Sound of Music and past single “Vogue”, not to mention its accompanying nutbar video which featured cameo appearances by the likes of Udo Kier, Sofia Coppola, and Debi Mazar. Udo Kier! –Allison Franks

13. “Borderline”

Madonna (1983)

Who knew a song about male chauvinism would be so fun to dance to? “Borderline” is that very song which helped push Madonna into the limelight on her debut release. For its time, the sentimental track proved itself as ahead of the curb blowing audiences away with her sober lyrics and complex synth harmonies. And with the help of its video, Madonna quickly became a role model for young girls. What teenage girl doesn’t aspire to be that care free and strong woman who’ll wreak havoc on your walls? –Allison Franks

12. “Frozen”

Ray of Light (1998)

The tribal mid-tempo ballad off Ray of Light remains one of Madonna’s most introspective hits. It’s the Material Girl doing Portishead and it’s brilliant. From the desolate Chris Cunningham-directed video to William Orbit’s silky production, the single should reek of late ’90s sensationalist pop, but it doesn’t. It’s an emotional piece that resonates with each listen; the elegant strings and digital percussion marry Madonna’s tragic pitch and let it soar. Lyrically, its mundanity comes across as a threat, a dark and sordid tale, making it one of her bleakest moments. As she told The New York Times: “Retaliation, revenge, hate, regret, that’s what I deal with in ‘Frozen’.” –Michael Roffman

11. “Lucky Star”

Madonna (1983)

Nursery rhymes were brought to a new level of sexual energy with Madonna’s “Lucky Star” back in 1983. Juxtaposing the male body with the stars up above was just the first trick up her sleeve as she chimed, “Come on shine your heavenly body tonight ‘cause I know you’re gonna make everything all right.” Then, she shyly remarks, “You may be my lucky star, but I’m the luckiest by far,” only sparking the innocent romance further. Who can resist that? Who? –Allison Franks