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As I wrote in my review of Erotica upon its 15th anniversary, “Waiting” is the ultimate masochism, one that’s entered into with full knowledge of what the emotional consequences will be. The very first lyric, “Well, I know from experience that if you have to ask for something more than once or twice, it wasn’t yours in the first place,” which Madonna utters with the same amount of interest a star of her stature might apply to buying a new pair of shoes, also happens to be one of the best opening lines to a pop song since “I guess I should have known by the way you parked your car sideways that it wouldn’t last.” Cinquemani


“Sky Fits Heaven”

This Ray of Light track is famous for being lyrically inspired by British poet Max Blagg’s 1992 poem “What Fits?” (later used in a Gap jeans commercial), but the song is a marvel not for Madonna’s new-age pontifications, but for its heavenly hook and William Orbit’s impeccable use of both analog and digital technologies, marked by expressive electric guitars and explosive drum fills constructed from tiny fragments of sound. Cinquemani


“I Want You”

Madonna’s haunting rendition of Marvin Gaye’s “I Want You” is, if not more soulful, infinitely more desperate than the 1976 original. The confidence and determination in Gaye’s voice is replaced here with the kind of naked vulnerability Madonna perfected on Bedtime Stories a year earlier. Her feat is no doubt aided by the song’s transformation from a conga-accented disco number into a more languid trip-hop track, courtesy of Massive Attack and producer Nellee Hooper. Cinquemani



From Marcel Proust to the more contemporary poet Carol Ann Duffy, Madonna has always drawn on literary influences in her lyrics, but it was of particular note on 1994’s Bedtime Stories, in which she artfully co-opted the work of George Herbert on “Love Tried to Welcome Me” and Walt Whitman on “Sanctuary.” On the latter, which musically draws inspiration from Herbie Hancock’s “Watermelon Man,” she boldly and cleverly pairs a passage from the Book of Genesis with Whitman’s “Vocalism,” effectively likening her existence prior to meeting her object of obsession to that of the Earth before God. Cinquemani


“Inside of Me”

With full, round production by Nellee Hooper, “Inside of Me” on the surface sounds like a warm, intimate sauna of slack slow jack built on a foundation of Aaliyah and the Gutter Snypes samples, but radiating a sensuality that’s all Madge. But like every track on her prior album, Erotica, this song’s breathy hedonism masks an inner devastation: Underneath those tear-stained suggestions of sex mournfully deferred is actually a heartfelt tribute to her mother. Staring down a crossroads in her career, Madonna couldn’t help but make grief sound like fornication. Henderson