Chartcrush Countdown Show 1999 Episode Graphic

1999 Top Ten Pop Countdown Podcast

Females rule as Latins invade, TLC returns, AutoTune appears and Total Request Live showcases Millennial Pop idols Britney, Christina, Backstreet and ‘NSYNC.

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Welcome to the Chartcrush Top Ten Countdown Show, I’m your host, Christopher Verdesi. Every week on Chartcrush, we do a deep dive into a year in Pop music and count down the top ten songs according to our recap of the weekly pop charts published at the time in the music industry’s top trade publication, Billboard magazine. This week on Chartcrush, we’re turning the clock back to 1999.

Well, in 1999, Mainstream Pop was suddenly fun and unpredictable again. In the early ’90s, Generation-X had finally broken through and reshaped the music landscape, just as its oldest members approached the age of 30, after a quarter century of Baby Boom dominance in Pop, Rock and R&B.

Not to say that music was stale and didn’t evolve in the Boomer years. It did, but within a box: a set of rules and boundaries that flowed from Boomer sensibilities. And no one really even knew there was a box until Hip-Hop, Alt (or “College”) Rock and Nu-Metal appeared and were clearly outside of it.

Now the big breakthrough for Gen-X sounds wasn’t some dramatic, bottom-up generational pop culture moment like Beatlemania; more like how a new accounting rule or OSHA mandate ripples through a company. In ’91, Billboard ditched its 50-year-old system of retail and DJ surveys and started basing the charts instead, on point-of-sale and airplay data from Soundscan and Broadcast Data Systems. And that turned out to be a kind of a BC/AD moment for the charts, where stuff that’d been thought of as “underground” for years was suddenly revealed to be the most popular music in the land.

How long had that been the case? Well, no way to know, but no sooner had Gen-X sounds come out into the sunlight than pre-teen and barely-teen Millennials (the children of Boomers), announced their presence with a wave of Bubblegum Pop like hadn’t been seen since the early ’70s. And fueling that wave, this was the first stuff Boomers had heard on Pop radio in years that didn’t take effort to understand, let alone like. Mom and dad approved. Then in the Fall of ’98, Millennials got their own after-school MTV show, Total Request Live with Carson Daly.

So Pop was back big. The Cold War was a memory. 9/11 hadn’t happened yet. The dot-com tech boom was booming. The Dow hit 10,000. Banks were handing out credit like it was candy. And the music industry was raking it in, especially now that songs didn’t have to be out as $5 singles, a dying format that was only really useful anymore for releasing Dance and Hip-Hop remixes in the CD era since vinyl 45s went extinct. “In response to the increasing number of singles that have not been made available at retail,” Billboard announced at the end of 1998, “airplay-only tracks now qualify for the chart.” About five years too late, but Hallelujah! The Hot100 was back, just in time for Millennial Pop!

#10 Jennifer Lopez – If You Had My Love

And just in time for The Latin Invasion, which took the charts by storm after Ricky Martin’s “Livin’ la Vida Loca” heralded its arrival in the Spring and was #1 for five weeks. “La Vida Loca” misses our countdown at #14, but the female chart newcomer who replaced Ricky Martin at #1 for the next five weeks in June and July actually had more to do with setting the stage for the Latin Invasion. In 1997 she played the title role in the hit biopic Selena, about a Tejano pop star who was shot and killed in 1995 by a deranged former fan club president, just as her career singing in English for the American charts was about to take off. “La Vida Loca” hit in April ’99, and then Jennifer Lopez’s debut single replaced Ricky Martin at #1, and it’s the #10 song as we kick off our countdown: “If You Want My Love.”

Jennifer Lopez’s first smash, the #10 song of 1999 here on our 1999 edition of the Chartcrush Top Ten Countdown Show, “If You Want My Love.” In the second half of ’99, after the one-two shot of Ricky Martin’s “Livin’ la Vida Loca” and “If You Want My Love” (a combined ten weeks atop the chart), there was a deluge of Latin Invasion hits: Enrique Iglesias’ “Bailamos!,” Marc Anthony’s “I Need to Know,” Lou Bega’s version of Pérez Prado’s “Mambo No. 5” and Shakira’s MTV Unplugged appearance and album (entirely in Spanish!), finally culminating with Santana’s comeback, “Smooth” in late October, which earned more chart points in calendar 2000 than 1999, so it’s in our 2000 countdown.

As for J-Lo, Pop stardom sure gave her budding movie acting career a boost. In January 2001 when The Wedding Planner co-starring Matt McConaughey hit theaters just ten days after her second album J.Lo dropped, she became the first person ever with the #1 album and the #1 film in the same week. And the album yielded three top-ten hits.

#9 Sixpence None the RicherKiss Me

Next up at #9, what one Millennial 90’s nostalgia writer described in a Buzzfeed feature as “your mom’s all-time favorite song:” a major hit on the Adult Alternative chart, but it was also a huge Hot100 Pop hit. It’s by an alternative Christian Rock trio from Texas, and it hit the chart at #90 for just a single week in November ’98 after it was in an episode of the WB network’s popular teen drama Dawson’s Creek. In January ’99 it showed up in theaters as the main theme of the teen romantic comedy She’s All That. But that movie didn’t have a soundtrack album, so it was included as the first track on the first Songs from Dawson’s Creek album, whereupon it re-entered the chart and rose into the top ten for 16 weeks, March into July, peaking at #2. Here is Sixpence None the Richer. “Kiss Me.”

Texas Indie Pop/Christian trio Sixpence None the Richer. “Kiss Me,” our #9 song as we count down the top ten from 1999 here on this week’s edition of the Chartcrush Top Ten Countdown Show. Songs from Dawson’s Creek was a top ten album and also included Paula Cole’s “I Don’t Want to Wait,” which had been used throughout the first season of the show and was on the charts for most of 1998. The group’s name “Sixpence None the Richer:” inspired by a line in British Christian apologist and Narnia author C.S. Lewis’ book Mere Christianity.

#8 MonicaAngel of Mine

Polls in the late ’90s were showing an uptick of religion in America. Was it pre-millennium apocalyptic jitters? Maybe fueled a bit by the near-hysteria that was brewing over the Y2K computer bug? Whatever, it had a big effect on pop culture. A Newsweek feature in late ’93 had reported on a new obsession with angels, and that inspired CBS to develop Touched by an Angel, which was the network’s top drama series in ’99. Another drama, 7th Heaven, went on to be the longest-ever running show on the WB network. Meanwhile, faith-based TV was getting big ratings on cable, and in music, Gospel’s market share was surging.

Suddenly, in December ’98, all at once, no fewer than five songs with the word “angel” in the title appeared on the Hot100 after nearly five years of not a one. And there were at least four “angel” songs on the chart through most of March 1999. Not minor hits, mind you: three were top tens and two of those were #1s: first the R. Kelly and Celine Dion duet “I’m Your Angel” in December ’98, then the biggest of them, our song at #8: the singer’s seventh top ten hit and her third #1, it’s Monica, “Angel of Mine.”

“Angel of Mine” at #5. Former Miss Thang teen star and Brandy collaborator Monica’s third and final #1 hit. She had quite a run from ’95, when she scored her first #1 at just 14 with “Don’t Take It Personal” (from Miss Thang) up to ’99: six more top tens including three #1s counting her duet with Brandy, “The Boy Is Mine.”

In the 2000s, she was all over TV, every one of her albums was top ten, and she put singles on the R&B chart every year up to 2019 including a trio of R&B top tens in ’09 and 2010. But none of that crossed over to the Hot100 after her final top ten hit in ’03 with “So Gone.”

Now, “Angel of Mine” was a cover of British R&B girl group Eternal’s 1997 U.K. hit. And that’s as close as any British artist got to the top of the U.S. charts in 1999. From The Beatles to the late ’80s, British acts averaged about six #1 songs on the U.S. charts every year. But in the early ’90s, that dwindled to one or two, and after the Spice Girls “Wannabe” and Elton John’s Lady Diana remake of “Candle in the Wind” in ’97, we didn’t see another Brit top the Hot100 until James Blunt’s “Beautiful” in 2006. The weekly Hot100 for April 27, 2002 was the first with no Brits since 1963.

Once America finally joined the Euro-Dance party in the late ’00s into the ’10s, Brits made a comeback and Coldplay, Taio Cruz, Adele, Sam Smith, Ed Sheeran and others did well Stateside , but nothing like Britannia’s dominance in the Boomer years.

#7 The Goo Goo Dolls – Slide

So in the intro I mentioned Billboard’s big, monumental change for the 1999 chart year: making the Hot100 a songs chart instead of a singles chart by expanding eligibility to airplay-only album tracks not out as physical singles. Well the group at #7 on our Chartcrush Top Ten Countdown for 1999 had the #1 Airplay song for an astonishing 18 weeks in 1998, “Iris,” which Billboard ranked #1 on a 2012 list of the top pop songs from 1992 to 2012. Surely, it would’ve been in the top ten, probably the top five, for 1998 if Billboard had changed that rule sooner, but at least their next big airplay smash was able to chart, and its our #7 song of 1999: Buffalo, New York’s Goo Goo Dolls, “Slide.”

Post-Grunge Alternative Rock trio Goo Goo Dolls with the #7 song of 1999, “Slide,” here on the Chartcrush Top Ten Countdown Show. It only peaked at #8 but was on the chart for 35 weeks, one of the longest chart runs of the year. And since it debuted on the Hot100 the week Billboard instituted the change to allow album cuts, December 5, 1998, it would’ve been even longer had it been out as a physical single. Goo Goo Dolls continued scoring Hot100 hits ’til 2008, and set the record for the most top tens in the history of Billboard’s Adult Contemporary chart in 2010, with 14.

#6 Deborah CoxNobody’s Supposed to Be Here

Our next artist at #6 was an “it” girl in Dance music at a time when Dance music was looming as large on the American charts as it would get before the EDM/Euro-Disco craze at the end of the ’00s into the 2010s. She’s had a whopping 13 #1’s on the Hot Dance Club Play chart from the ’90s up to 2017. From her second album One Wish, this was her first top ten on the Hot100. Raised in Toronto by her Guyanan parents, it’s Deborah Cox, “Nobody’s Supposed to Be Here.”

Deborah Cox. “Nobody’s Supposed to Be Here,” #6 on our Chartcrush Top Ten Countdown for 1999: #1 for 14 weeks on the Hot R&B/Hip-Hop Songs chart, which set a new record for that chart. On the Hot100 it got stuck at #2 for eight straight weeks in December ’98 into January ’99; six of them behind the same song at #1, the aforementioned R. Kelly and Celine Dion duet, “I’m Your Angel.” And that was almost a record (longest stays at #2). Some radio stations preferred the upbeat Dance remix of the song by Puerto Rican producer Hex Hector.

Cox had no significant Pop hits after 1999, but she stayed hot on the Dance Club Play chart for years. She’s been married to her high-school sweetheart since 1998. They have three kids.

#5 Christina AguileraGenie in a Bottle

Now if this were the game show Family Feud at the turn of the millennium and the question was “name a female Millennial Pop star,” the top two “survey says” answers would be the pair of super-sexy teen-blonde chart newcomers whose debut smashes are back-to-back at numbers five and four in our countdown. They were both alumni of Star Search and The Disney Channel’s early ’90s Mickey Mouse Club reboot. And since they were vying for the same audience, their rivalry was tabloid catnip: 1999’s burning pop culture question, endlessly hyped on MTV and elsewhere in the media.

But it wasn’t a rivalry until the second song followed the first to the top of the chart, and Britney Spears’s debut, rocking a midriff-baring schoolgirl uniform asserting that she’s not so innocent on “…Baby One More Time,” was first in January, followed by our #5 hit in July: a sexy, innuendo-filled song that had its singer having to defend her innocence all summer. Britney was the good girl; Christina Aguilera, the bad girl thanks to 1999’s big summer hit, Christina’s “Genie in a Bottle.”

Squeaky clean ’80s Teen-Pop star Debbie Gibson was horrified by “Genie in a Bottle’s” sexual lyrics, and she wasn’t alone. Besieged with pointed questions along those lines all summer with the overlay of the ginned up rivalry vs. “good girl” Britney, 18 year-old Christina Aguilera had to repeat ad nauseum some version of “It’s not about sex, it’s about self-respect! I’m the genie in the bottle; you gotta rub me the right way!” But even with that helpful context, she had to go back and re-record lyrics like “hormones racing” to “heart-beats racing,” “rub me the right way” to “treat me the right way” to pass muster in some countries.

It didn’t hurt her though. After “Genie in a Bottle,” the rocket ship Christina Aguilera continued to ascend. Her next single, “What a Girl Wants,” was the first #1 of calendar 2000 and then she scored another top ten summer hit with her cover of All-4-One’s ballad from the film Space Jam, “I Turn to You,” followed by the star-studded remake of “Lady Marmalade” from the era-defining jukebox musical Moulin Rouge in ’01, on which Christina was the lead artist along with Missy Elliott, Pink, Mýa and Lil’ Kim.

#4 Britney Spears…Baby One More Time

Britney did okay too. “Oops! I Did It Again,” her big Y2K hit, peaking at #9. But that’s getting ahead of ourselves. Let’s rewind. At #4 on the year 1999, beating Christina by literally just one point, 1,271 to 1,270, in our Chartcrush ranking system, the artist and her #1 debut single that emphatically announced the arrival of the Millennial generation.

And it was the only song in our 1999 top ten that debuted in the top 20. Up to 1999, fewer than 50 new artists in Hot100 history had done that, and the list reads like a chronology of teen sensations. Well, no exception here: the minute she appeared on TV screens in that aforementioned schoolgirl outfit, the future of Pop in the Y2K decade became crystal clear. Bubblegum was back, but it was never as sexy or broadly appealing as our #4 song, again, beating rival Christina Aguilera by just a single point (for all intents and purposes a tie), Britney Spears’ “…Baby One More Time.”

“…Baby One More Time,” 16-year-old Britney Spears, the first on the calendar of the three brand new female acts in the top ten, along with Christina Aguilera and J-Lo, whose chart debuts went to #1. And I’ve got to mention a fourth that didn’t make our top ten. Lauryn Hill’s first solo single, “Doo Wop (That Thing)” was only the tenth song ever to debut at #1, but the very first by a new artist. Of course, Hill had just wowed everyone with her smash cover of Roberta Flack’s “Killing Me Softly” in 1996, but that was with her group, The Fugees, not as a solo act.

Now the Britney vs. Christina rivalry never really went away. Coming out of 1999 into the early ’00s, Christina dominated with her aforementioned string of hits, but then Britney flipped the script in the second half of the decade starting with “Toxic” in ’04.

#3 Cher – Believe

At #3 on our 1999 Chartcrush Top Ten Countdown, the song that was Billboard’s #1 song of the year, by a singer whose first appearance on the charts was in 1965. At nearly 53, she became the oldest woman to sing lead on a #1 hit, shattering the record previously held by Grace Slick, formerly of The Jefferson Airplane, who was 47 when Starship’s “Nothing’s Gonna Stop Us Now” peaked at #1 in 1987.  Here is the never-irrelevant Cher with her 1999 dance-pop hit, “Believe.”

It’s not often that a piece of behind-the-scenes studio technology becomes a celebrity, but that effect you hear on Cher’s vocals in that song? “Believe” was one of the first commercial recordings to use Auto-Tune, a digital audio software plugin developed to make subtle corrections to off-pitch vocals. But if you turn up all the controls to maximum, you get that artificial glitchy sound now known as “The Cher Effect” thanks to “Believe.” Music people always gonna turn those knobs up to ten, right?

Well, since then, top rappers like T-Pain and Lil Wayne have made The Cher Effect an integral part of their signature sounds. It became so ubiquitous in Hip-Hop that in 2009, Jay-Z titled the lead single off his album The Blueprint 3 “D.O.A. (Death of Auto-Tune).” In 2010, Time magazine included Auto-Tune in its list of “The 50 Worst Inventions.” But back in ’99 when people heard it for the first time on our #3 song, Cher’s “Believe,” it got everyone’s attention straight away.

#2 TLCNo Scrubs

By now you’ve undoubtedly noticed the preponderance of female acts in our Chartcrush Top Ten Countdown of 1999’s top hits. It was the year-of-the-woman like no other at the top of the Pop charts: the first and to-date only year in chart history with such a lopsided split in favor of the ladies.

Now that we’re down to #2, I’m not really spoiling anything by revealing to you that nine of the top ten songs of 1999 are sung by women, and all of the year’s top six hits are by female artists. Our #2 song was also #2 on Billboard’s year-end ranking, and the #1 most played song of the year on the radio, according to Billboard’s year-end Airplay chart.

They were the most successful Girl Group of the ’90s, but hadn’t put an album out since their 1994 Diamond certified CrazySexyCool. Diamond, the Recording Industry Association of America’s designation for sales of ten million, or ten times Platinum. So after five years, FanMail was one of the most anticipated releases by any artist. Their eighth top ten hit since 1992 and one of their most iconic songs, it’s TLC, “No Scrubs.”

So what’s a cash-strapped hombre (or as TLC calls you, a “scrub”) supposed to do in the “No Scrubs” era? Well, there’s only one thing to do, I suppose: put romance on the back burner until you make your first million! Or, I guess you can write an answer song like Yonkers, New York Hip-Hop duo Sporty Thievz did. Their song about substandard women, “No Pigeons,” peaked at #12 on the Hot100 right in the middle of TLC’s chart run with the song we just heard, “No Scrubs,” the #2 song on our 1999 Chartcrush Top Ten Countdown.

Each of TLC’s three albums through the ’90s reflected the rapid evolution of R&B in the Hip-Hop era. They were the first Girl Group that had a rapper! The other big hit from their 1999 FanMail album was a timely anti-body-shaming song done in an Acoustic Pop style inspired by the success of the all-female Lilith Fair festival tour. That song, “Unpretty,” just misses our countdown at #11. Billboard named TLC the top Hot100 artist of 1999 on the combined strength of just those two hits, plus the Techno-R&B advance-single, “Silly Ho,” which failed to crack the top 40, probably because most radio stations wouldn’t touch a song titled “Silly Ho,” even in 1999.

Despite friction in the group, TLC were working on a fourth album in ’02, when Left Eye crashed her rented SUV in Honduras and was killed. Tionne “T-Boz” Watkins and Rozonda “Chilli” Thomas reunited as TLC for special appearances in the 2000s, but it wasn’t until 2015 that they attempted a real comeback with a new album and tour.

#1 702 – Where My Girls At?

Now get this: the #1 hit of 1999 according to our Chartcrush ranking is a song that was offered to TLC, but they passed on it! So another girl group snapped it up, and its 42 week run on the Hot100, peaking at #4 for a week in June, was the longest of the year, extending several weeks past Billboard’s November 27th cutoff date for the 1999 chart year and into 2000. As such it’s one of the many examples of songs throughout chart history that don’t get their due on any Billboard year-end chart because their ranking points are divided between two years.

Nothing at all Billboard can do about that since they have to get their year-end charts out in December, before New Years. But fortunately, Chartcrush is here to set the record straight, with the luxury of hindsight, by factoring every song’s full chart run. And when you do that in this case, what was Billboard’s #11 song of 1999 gets bumped all the way up to #1. In the top ten for 19 of its 42 weeks, racking up those big points, here’s 702, written and co-produced by rapper Missy “Misdemeanor” Elliott, the anti side-chick anthem, “Where My Girls At?”

Girl group 702, named after the area code in Vegas, where they were from: their second top ten hit, “Where My Girls At?” For their follow-up in 2003, they worked with Pharrell Williams and his production crew The Neptunes, and despite a star-studded roster of guest appearances on the album, it was a commercial disappointment with no hit singles, and 702 went on to solo careers.


Now we have a couple minutes left, and lots of worthy honorable mentions for 1999.

Destiny’s Child’s very first #1 hit, “Bills, Bills, Bills” was the lead single from their smash album The Writing’s on the Wall.

“Bills, Bills, Bills” was our #26 song.

The male side of the 1999 Teen Pop explosion, Backstreet Boys and NSYNC produced four top tens in Pop’s most female-dominant year ever.

Backstreet Boys’ “I Want It That Way,” our highest ranking Boy-Band hit of the year at #13.

And there are three cuts that were in the top ten on Billboard’s year-end Hot100, but didn’t make our countdown. One I mentioned earlier in the show: the song that broke the Latin Invasion wide open.

Ricky Martin’s “Livin’ la Vida Loca” was Billboard’s #10 song of 1999. It was #14 on our Chartcrush ranking.

After their song “Fly” was #1 on the Airplay chart for four straight weeks in 1997, critics advised Sugar Ray to enjoy their 15 minutes of fame because surely, they were destined for one-hit-wonder status. Well they titled their next album 14:59, one second shy of 15 minutes on the fame clock. Get it?

“Every Morning” defied Sugar Ray’s naysaying critics: #8 on Billboard’s year-end Hot100; #12 on our Chartcrush ranking.

Whitney Houston foreshadowed (or maybe caused) the end of the ’90s Pop Diva Era by moving away from Pop ballads and going full-bore R&B on her first studio album in eight years, and like 702’s “Where My Girls At,” the album’s biggest hit was a song that was offered first to TLC, and rejected!

“Heartbreak Hotel” featuring Faith Evans and Kelly Price: Billboard’s #4 song of 1999, one of four 1999 hits, including three top tens, from Whitney Houston’s My Love Is Your Love album. If you add up all that chart action, Whitney comes out 1999’s top Hot100 Artist. “Heartbreak Hotel” was #18 on our Chartcrush ranking.

Alas, we are out of time and that’s gonna have to be a wrap for our 1999 edition of the Chartcrush Top Ten Countdown Show, but I want to thank you for listening! I’ve been your host, Christopher Verdesi. Be sure to check out our website, There you’ll find written transcripts and streaming links for this and other Chartcrush countdown shows, plus chart run line graphs and other phat (with a “ph”) extras. We count down a different year every week on this show, from the very beginning of the charts in the ’40s all the way up to the present, so tune in again next week, same station and time, for another edition of Chartcrush.

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