1. Santana feat. Rob Thomas, “Smooth”
Released as the first single from Santana’s album Supernatural, the song built huge momentum over the summer before becoming, not only one of the biggest hits of that year (spending 12 weeks at No. 1 on the Billboard Hot 100), but also the decade — staying in the top-ten of the Billboard Hot 100 for 30 weeks.
2. Christina Aguilera, “Genie In A Bottle”
The sexually-suggestive single was the first single released from Christina Aguilera’s self-titled debut album. The song stayed atop the Billboard Hot 100 for five consecutive weeks.
3. Jennifer Lopez, “If You Had My Love”
Jennifer Lopez’s debut single quickly climbed up the charts to No. 1 on the Billboard Hot 100 — dethroning Ricky Martin’s “Livin’ La Vida Loca” — where it would remain atop for five weeks.
4. Destiny’s Child, “Bills, Bills, Bills”
The first single from Destiny’s Child’s blockbuster album, The Writing’s on the Wall, was also their first No. 1 single.
5. Pearl Jam, “Last Kiss”
The song was originally released as a fan club exclusive single in Christmas 1998, but was eventually serviced to radio in early ‘99. The song’s popularity on radio led to the band releasing it as a commercial single, along with B-side “Solider of Love,” in June.
The song peaked at No. 2 on the Billboard Hot 100 and remain’s Pearl Jams’ biggest charting hit to date.
6. 702, “Where My Girls At?”
Written and produced by Missy Elliott, “Where My Girls At?” reached No. 4 on the Billboard Hot 100 and No. 3 Hot R&B.
7. Len, “Steal My Sunshine”
The single, which was originally included on the Go soundtrack, peaked at No. 9 on the Billboard Hot 100 and No. 5 on the Modern Rock Tracks.
8. Sugar Ray, “Someday”
The second single released from Sugar Ray’s 1999 album 14:59, peaked at No. 7 on both the Billboard Hot 100 and the Hot Modern Rock Tracks.
9. Madonna, “Beautiful Stranger”
“Beautiful Stranger” was written by Madonna and William Orbit — who produced her 1998 album Ray of Light — specifically for the Austin Powers: The Spy Who Shagged Me soundtrack. While the song was never released as a commercial single (it was an album exclusive), it still managed to reach No. 19 on the Billboard Hot 100.
The song also won a Grammy Award for Best Song Written for a Motion Picture, Television or Other Visual Media at the 2000 Grammys.
10. Smash Mouth, “All Star”
A couple of years before the “All Star” became synonymous with Shrek, it actually served as the theme song to another film, the criminally underrated Mystery Men. In fact the music video features cameos from the film’s stars, William H. Macy, Ben Stiller, and Janeane Garofalo.
The single peaked No. 4 on the Billboard Hot 100.
11. Will Smith, “Wild Wild West”
The official theme song to Will Smith’s ode to steampunk, the song reached No. 1 on the Billboard Hot 100.
The song also has the distinction of winning the Razzie Award for Worst Original Song.
12. Ricky Martin, “Livin’ La Vida Loca”
Ricky Martin’s breakthrough crossover single was his first No. 1 song on the Billboard Hot 100, where it remained for five weeks (probably due to moms everywhere who couldn’t get enough of that song and Ricky).
13. Whitney Houston, “It’s Not Right but It’s Okay” (Thunderpuss Remix)
Whitney Houston’s third single from her 1998 album, My Love Is Your Love, became a big hit — reaching No. 4 on the Billboard Hot 100 and No. 1 on the Hot Dance Club Songs — after the Thunderpuss remix version of the track was released.
14. LFO, “Summer Girls”
LFO (aka the Lyte Funky Ones) for better or worse, had one of the biggest hits of the summer of 1999, which they achieved by cleverly (not really) name checking Abercrombie and Fitch — and Chinese food.
The song peaked at No. 3 on the Billboard Hot 100.
15. Backstreet Boys, “I Want It That Way”
“I Want It That Way,” was the first single from Backstreet Boys’ third U.S. album, Millennium, the cleverly crafted pop song — which had an equally clever TRL friendly music video — was the perfect summer love song. The song surprisingly only reached No. 6 on the Billboard Hot 100. But the momentum the song built helped make Millennium become the best-selling album of 1999.
But above all, it really is a good song!