40. Luscious Jackson – “Ladyfingers”
By 1999, Beastie Boys offshoot Luscious Jackson had shed keyboardist Vivian Trimble and released their album Electric Honey as a trio before quietly disbanding in 2000. The band, known for their hypnotic basslines, entrancing harmonies, and hip-hop beats, struggled to find a lasting place in the broad musical landscape that, by decade’s end, consisted of boy bands, pop stars and nü-metal acts with questionable chin braids. Luscious Jackson’s last hurrah was “Ladyfingers,” Electric Honey‘s seductive, understated lead single, which carved out a prominent place in VH1’s rotation and was featured in a Buffy the Vampire Slayer episode—a high honor for any ’90s band. — MAGGIE SEROTA
39. Fountains of Wayne – “Denise”
On “Denise,” Fountains of Wayne rhyme “Liberty Travel” with “heart made of gravel,” pausing mid-line as if to remark at the sheer cleverness of the writing. That is the litmus test for “Denise,” or really Fountains of Wayne in general, and maybe power-pop as a whole: Does such a songwriting trick capture your heart? Or fill it with stone so leaden one wishes it were just gravel? That line is also, as the band admitted, pretty much the reason “Denise” was written. But the rest is no-brainer stuff: a gushing homage to ’80s power-pop and women with offbeat quirks (here, a lavender Lexus, which, of course, rhymes with “Texas”). The band would refine this dynamic further with “Stacy’s Mom” a few years later. — KATHERINE ST. ASAPH
38. 311 – “Come Original”
“Come Original” marks the moment when the cool kids stopped caring about 311 and 311 stopped caring about the cool kids. After a decade of grinding it out as your favorite skater’s favorite rap-rock band, 311’s fifth album, Soundsystem, traded slam dancing for noodle dancing and never looked back. Now, 20 years after 311 jumped the S.S. Alt Rock for Hippy Island, they are elder statesmen of their own reggae-rock subculture and one of the only bands on this list that managed to age gracefully. — SEAN MALONEY
37. Beth Orton – “Stolen Car”
Beth Orton’s career is a bit of an anomaly. After breaking out as a vocalist with the Chemical Brothers and William Orbit, she carved out a vaguely folk, downtempo, and alt-rock niche that never totally resembled her singer-songwriter peers, whether poppy fare or Lilith Fair. But Beth Orton definitely didn’t resemble the sweatier, bro-ier stuff on the Modern Rock charts that “Stolen Car” cracked. Why is this here alongside the Bizkits and Bawitdabas? Even Orton was bemused, as she told Billboard: “[Ben Harper’s part] is a nice piece of guitar, and Americans love guitar, right?” It is a nice piece of guitar, processed and fuzzed to sound uncannily like a cello even during its solo; it lends its own kind of rock heft to an otherwise placid folk track, going big by getting wistful. And Orton’s line, while precisely observed—”it’s little things like this that matter to me,” is the opposite of 75% of this list—has plenty of its own forward momentum and internal percussion. — KATHERINE ST. ASAPH
36. Pearl Jam – “Last Kiss”
A band whose quixotic impulses endeared them to fans, Pearl Jam was, by 1999, nevertheless shedding the mass audience that had made Ten the best-selling rock album of the Cobain Era. A quickie Wayne Cochran cover recorded for a Kosovar refugee benefit album became their first—and only —Top 5 hit. “You can try album after album to write a hit and spend months getting drum sounds and rewriting lyrics,” guitarist Stone Gossard told The Boston Globe, “or you can go to a used record store and pick out a single and fall in love with it.” Like Bruce Springsteen recording “Dancing in the Dark” out of pique – a hit that also peaked at #2 – Pearl Jam were convincing under pressure. When Eddie Vedder wonders, “Where, oh, where, can my baby be?” it trembles with an adolescent yearning that’s the match of Backstreet Boys’ “I Want It That Way,” also a hit that summer. — ALFRED SOTO