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The 98 Greatest Songs of 1998: Critics' Picks

31. Madonna, "Frozen" (No. 2, Hot 100)
The lead single from Madonna’s seventh album, Ray of Light, “Frozen” is a masterpiece of William Orbit-produced electro-pop that has arguably aged better than any of her hits since. The track was released just a few months before Madonna’s 40th birthday -- and less than a year and a half after she’d become a mother for the first time -- and both the spare lyrics (about a cold-hearted lover) and the cool, lush, and enveloping interplay of synthesizers, strings, and Eastern percussion showcase a wiser, more mature Madonna, one still at the top of her game. “If I could melt your heart,” she sings in the chorus. With “Frozen,” she does. -- FRANK DIGIACOMO

9. Madonna, "Ray of Light" (No. 5, Hot 100)
The world seemed to be tiring of global superstar Madonna by the late '90s, so naturally, she responded by simultaneously re-conquering the planet and reaching new creative peaks. Working with British DJ-producer William Orbit and drawing on a 1971 folk song (Curtiss Maldoon's "Sepheryn") for lyrics, Madge gave radio its most joyous, ebullient and life-affirming dance banger since, well, maybe her own "Into the Groove" more than a decade prior. Yeah, the cool kids had been raving for years, but it took a trendsetting 39-year-old mom (who just happened to have 11 No. 1s to her name) to crack open the top 40 for what was then called electronica's eventual pop takeover. -- J.L.

The 50 Greatest Deep Cuts of 1998: Critics' Picks

39. Madonna, "Swim" (Ray of Light)
Madonna’s Ray of Light album was about her spiritual awakening, and “Swim” reflected the emotional weight that often came with seeing that journey through. The song’s ethereal production bellows and crashes like the ocean’s waves as she tries to search for a safe space in a chaotic world. The melancholy of “Swim” is a result of its tragic backstory: Madonna received a phone call that her close friend Gianni Versace had been murdered on the same day she recorded the track. The sorrow heard through Madonna’s deep vocals is unmistakable. -- BIANCA GRACIE

10. Madonna, "Shanti / Ashtangi" (Ray of Light)
No one was asking Madonna for a Hindu Sanskrit prayer set to club music in 1998, but she was so on top of her game with Ray of Light that "Shanti/Ashtangi" makes it sound perfectly reasonable that spiritual enlightenment is best found on a booming dancefloor. With text adapted from Indian philosopher Shankara and pronunciation assists from Sanskrit expert Vagish Shastri, Madge made inner peace and chilly techno seem like the most strangely satisfying odd couple around – at least until Rush Hour opened that fall. -- J.L.