27. Sixpence None the Richer, "Kiss Me" (No. 2, Hot 100)
"Kiss Me" is mushy and cute and sweet and vulnerable -- it sounds like falling for someone, which is why it connected with Dawson's Creek viewers, just about every teen movie within two years of the millennium, and countless proposals in the years since. Sixpence None the Richer's breakthrough hit spent 16 weeks in the Hot 100's top 10, peaking at No. 2 in May of '99 -- the Nashville folk-pop outfit's only non-cover song to reach a Top 40 audience. But it's lived on in the language of falling in love (and wedding cover bands) so well, it still feels like it's riding off into the sunset. -- C.P.
26. Mariah Carey feat. Jay-Z, "Heartbreaker" (No. 1, Hot 100)
Few artists did more to bridge the gap between pop and hip-hop in the ‘90s than Mariah Carey, who made featured guest appearances by rappers a regular part of the diva playbook. She’d been doing it for years by the time she teamed up with Jay-Z for the lead single off Rainbow, but “Heartbreaker” -- built around a sample of Stacy Lattisaw’s 1982 novelty hit “Attack of the Name Game” -- perfected the formula with her swooning vocals and his playful rhymes. In perhaps one of pop culture’s luckiest close calls, Carey reportedly planned to put “Heartbreaker” on her ill-fated Glitter soundtrack, until the project got delayed. But the song ended up getting its own mini-movie treatment anyway: The “Heartbreaker” music video, one of the most expensive videos ever made at the time, finds Carey coming to blows with devious romantic rival named Bianca (also played by Carey), in a fight scene so iconic Carey has been recreating it on her current world tour. -- N.F.
25. Celine Dion, "That's the Way It Is" (No. 6, Hot 100)
As a singles artist, Celine Dion’s stardom in the U.S. almost exclusively resided in the 1990s; the Canadian superstar has collected 10 top 10 hits on the Hot 100 chart, beginning in 1990 with “Where Does My Heart Beat Now” and ending at the turn of the century with “That’s the Way It Is." When the latter was released in '99 as a new single on a greatest hits compilation, it swerved away from the high drama of Dion’s world-conquering then-recent hit “My Heart Will Go On,” and toward something much more pillowy, more in the vein of light adult-contemporary fare by country-pop artists like Faith Hill and Shania Twain. The slight turn was masterful: “That’s the Way It Is” embraces the intrinsic corniness of its self-affirming message, as Dion delivers plenty of winks in between a typically stellar vocal performance. She’d never impact pop radio quite the same way after this, but what a blissful way to go out. -- J. Lipshutz
24. Red Hot Chili Peppers, "Scar Tissue" (No. 9, Hot 100)
Having weathered two motorcycle accidents and the thorny departure of mid-'90s guitarist Dave Navarro, the Red Hot Chili Peppers were desperately in need of a rebound by ‘99. The wistful, confessed “Scar Tissue” was the perfect comeback, mixing drawled lyrics about loneliness with subtle motivation (“I’ll make it to the moon if I have to crawl”) and one hell of a guitar solo from returning axeman John Frusciante. In his autobiography (also titled Scar Tissue), bandleader Anthony Kiedis looked back on the song as a “phoenix-rising-from-the-ashes vibe,” and he was right -- “Scar Tissue” won a Grammy and served as the lead single off Californication, the similarly Grammy-winning LP that would re-establish RHCP as superstars. -- T.C.