’90s No. 2s Revisited: 1999

’90s No. 2s Revisited: 1999

We conclude our ’90s No. 2s Revisited series with the last year of the decade, and in keeping with what made the decade so special, variety abounds. The runner-up hits from 1999 represented acts gaining popularity as well as those on the decline, and covered the hot genres of the time — Pop, Alternative Rock, R&B, Hip-Hop and Latin. Enjoy!

“Heartbreak Hotel,” Whitney Houston featuring Faith Evans and Kelly Price
3 weeks at No. 2, starting March 20, 1999
Blocked by: “Believe,” Cher

The No. 2 spot was not familiar territory for superstar Whitney Houston, who’d racked up 11 No. 1 songs by 1999, and in fact “Heartbreak Hotel” was the singer’s only song ever to peak at No. 2. It’s an OK mid-tempo R&B song but not a particular standout among Houston’s amazing discography, although it was quite popular and landed in the No. 4 spot on Billboard’s year-end tally, the best showing of any ‘99 single not to reach No. 1. Collaborator Faith Evans had reached No. 1 with “I’ll Be Missing You” in 1997, and Kelly Price’s biggest hit outside “Heartbreak Hotel” was 1998’s “Friend Of Mine” (peak: 12). “Heartbreak Hotel” was the lead single off Houston’s multiplatinum album My Love Is Your Love, which produced two more Top 5 hits, “It’s Not Right But It’s Okay” (peak: 4) and the title track (peak: 4). She would find herself ever-less popular on Top 40 radio in the 2000s before accidentally drowning in a bathtub in 2012 at age 48.

“Kiss Me,” Sixpence None the Richer
1 week at No. 2, starting May 1, 1999
Blocked by: “No Scrubs,” TLC

Unknown band Sixpence None the Richer scored a massive hit in 1999 with the upbeat Pop/Rock ditty “Kiss Me.” Although their name suggests British origins, they’re actually from Texas. “Kiss Me” was a very nice song we enjoyed hearing on the radio, which is good news since it was on all the time, and it was prominently featured in the classic makeover scene in the teen romance She’s All That. Sixpence None the Richer would have two more minor hits: a 1999 remake of The La’s’ “There She Goes” (peak: 32) and a 2003 remake of Crowded House’s “Don’t Dream It’s Over” (peak: 78).

“Last Kiss,” Pearl Jam
1 week at No. 2, starting June 26, 1999
Blocked by: “If You Had My Love,” Jennifer Lopez

Grunge legends Pearl Jam found themselves with a surprise crossover hit in the summer of 1999 with their cover of “Last Kiss,” originally recorded by its songwriter Wayne Cochran in 1961 but better known as a No. 2-peaking song for J. Frank Wilson and the Cavaliers in 1964. Although Pearl Jam were darlings of MTV and had three No. 1 albums during the ’90s, they didn’t have (or particularly want) much Top 40 crossover success, so hearing Eddie Vedder’s voice on Pop radio stations in 1999 was a little odd. “Last Kiss” is an extremely weird song, as the major chord progression and poppy drumbeat belie depressing lyrics about a teenage boy whose girlfriend dies in a car accident while he’s driving them to a date. Pearl Jam did the track for a charity album to benefit Kosovo War refugees.

“Tell Me It’s Real,” K-Ci & JoJo
1 week at No. 2, starting Aug. 14, 1999
Blocked by: “Genie In A Bottle,” Christina Aguilera

Prior to 1999, K-Ci & JoJo, half the R&B quartet Jodeci, had scored two No. 1 hits, first as featured vocalists on 2Pac’s “How Do U Want It” in 1996, then on their own with the gorgeous wedding-appropriate ballad “All My Life” in 1998. “Tell Me It’s Real” was in the vein of the latter, but used auto-tune to an extent that annoyed us and detracted from the pretty elements of the song. Also it felt like a puzzling production choice given that these singers were very talented and didn’t need their voices processed. They’d go on to have one more hit, the similar-sounding “Crazy” (peak: 11) in 2001.

“She’s All I Ever Had,” Ricky Martin
2 weeks at No. 2, starting Sept. 25, 1999
Blocked by: “Unpretty,” TLC

After making a giant splash with his up-tempo chart-topping hit “Livin’ La Vida Loca,” Ricky Martin showed a softer side with the ballad “She’s All I Ever Had.” We thought this song was lovely. He’d go on to have a few more hits afterward, including the upbeat “Shake Your Bon-Bon” (peak: 22), the terrific “Private Emotion” featuring Meja (peak: 67), “She Bangs” (peak: 12) and a duet with Christina Aguilera, “Nobody Wants To Be Lonely” (peak: 13), one of our favorite songs of 2001.

“Music Of My Heart,” *NSYNC & Gloria Estefan
1 week at No. 2, starting Oct. 16, 1999
Blocked by: “Heartbreaker,” Mariah Carey featuring Jay-Z

An unlikely collaboration for the Meryl Streep film Music of the Heart, “Music Of My Heart” features Gloria Estefan, whose popularity was waning, and *NYSNC, whose popularity was growing, on the Diane Warren-penned ballad. By this point, Estefan had achieved three No. 1s, but hadn’t had a Top 20 hit in almost five years when “Music Of My Heart” climbed to No. 2. *NSYNC, meanwhile, were staples on MTV’s TRL and had achieved two Top 20 hits, but their most popular singles were yet to come, including their only No. 1 hit, “It’s Gonna Be Me” in 2000. All of Diane Warren’s music is lovely, this included. But not all of it is particularly consequential, this included.

“Satisfy You,” Puff Daddy featuring R. Kelly
3 weeks at No. 2, starting Oct. 30, 1999
Blocked by: “Smooth,” Santana featuring Rob Thomas

“Satisfy You” heavily rips off Luniz’s 1995 hit “I Got 5 On It” (peak: 8), which itself heavily rips off Club Nouveau’s 1987 hit “Why You Treat Me So Bad” (peak: 39). (Gotta be honest, throughout this blog we’ve always sighed when we had to review Puff Daddy’s songs, because they’re so full of samples, it’s exhausting to explain each song’s origin.) This track was, oddly, the only charting song off Puff Daddy’s sophomore album, Forever. It’s OK. Like all his songs, to the extent it’s good, it’s only good because he’s stealing good components from better songs. He tends to recycle rather than elevate, in our opinion.

“Back At One,” Brian McKnight
8 weeks at No. 2, starting Nov. 20, 1999
Blocked by: “Smooth,” Santana featuring Rob Thomas

The last song to peak at No. 2 in the ’90s was the beautiful ballad “Back At One” by singer-songwriter-pianist Brian McKnight, who spent eight weeks patiently in the runner-up spot on the Billboard Hot 100. McKnight scored a few hits in the ’90s, the biggest being his 1993 duet with Vanessa Williams, “Love Is” (peak: 3), and his solo debut shortly thereafter, “One Last Cry” (peak: 13). He also had a big radio hit in 1998 with “Anytime,” one of our favorite songs of that year, which was ineligible to chart because it wasn’t released as a physical single. “Back At One” was almost an echo of the Adult Contemporary fare that rules the beginning of the decade but had fallen out of favor. Its success pleasantly surprised us.

– John

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