Top 10 Pop Songs of 1999

01
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10. Sugar Ray - "Every Morning"

Sugar Ray Every Morning
Sugar Ray - "Every Morning". Courtesy Atlantic

The feel-good music of Newport Beach, California band Sugar Ray is one of the pure pleasures of 90s pop music. This tale about a girlfriend who "has a halo hanging from the corner" of her four-post bed is instantly recognizable and memorable. It was the band's second top 10 pop hit single following their 1997 #1 smash "Fly." "Every Morning" was a radio smash hitting the top of the alternative, mainstream pop, and adult pop radio charts.

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02
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9. Marc Anthony - "I Need To Know"

Marc Anthony I Need To Know
Marc Anthony - "I Need To Know". Courtesy Columbia

The success of Ricky Martin early in 1999 opened the door for other Latin pop vocalists. One of the most talented was Marc Anthony. "I Need To Know" was the perfect vehicle to land his gorgeous voice on the mainstream pop radio airwaves. Marc Anthony had already put together a string of nine top 10 Latin hit singles. "I Need To Know" earned a Grammy Award nomination for Best Male Pop Vocal Performance and won the Latin Grammy for Song of the Year.  In 2000 Marc Anthony returned to the pop top 10 with the hit "You Sang To Me."

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03
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8. Backstreet Boys - "I Want It That Way"

Backstreet Boys I Want It That Way
Backstreet Boys - "I Want It That Way". Courtesy Jive

"I Want It That Way" is simply one of the great ballads in pop music history. It gave the Backstreet Boys the perfect opportunity to let their polished voices shine and it became one of their biggest hits. "I Want It That Way" was the group's fourth top 10 pop hit. It received Grammy Award nominations for Record and Song of the Year. Sweden's Max Martin co-wrote and co-produced the song.

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04
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7. Whitney Houston - "It's Not Right But It's Okay"

Whitney Houston It's Not Right But It's Okay
Whitney Houston - "It's Not Right But It's Okay". Courtesy Arista

By the time the 90s headed toward a close, it had been eight years since the last new Whitney Houston studio album. Music industry legend Clive Davis coaxed her back into the studio for a new set and the resulting album My Love Is Your Love has some of her best work. "It's Not Right, But It's Okay" is a hard-hitting anthem for women on the way out of relationships that sounded great on the radio or on the dancefloor. The song reached the top five on the Billboard Hot 100 and a well-received remix helped propel the song to the top of the dance chart. "It's Not Right But It's Okay" earned Whitney Houston a Grammy Award nomination for Best Female R&B Vocal Performance.

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05
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6. TLC - "No Scrubs"

TLC No Scrubs
TLC - "No Scrubs". Courtesy LaFace

The R&B trio TLC electrified the pop music world with their phenomenal album Crazysexycool released in 1994. Then it was a long 5 year wait for the next installment. Fortunately, Fan Mail was nearly as good as its predecessor. "No Scrubs," the leadoff single, is picture perfect late 90s R&B. It became TLC's third #1 pop hit single and earned them their second Grammy Award nomination for Record of the Year. "No Scrubs" also topped the R&B singles chart.

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06
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5. Lauryn Hill - "Doo Wop (That Thing)"

Lauryn Hill Doo-Wop That Thing
Lauryn Hill - "Doo Wop (That Thing)". Courtesy Columbia

After the far too early breakup of the Fugees, the music world waited impatiently for Lauryn Hill's first solo effort. The wait was worth it. The Miseducation Of Lauryn Hill is one of the top albums of the decade and "Doo Wop (That Thing)" is a brilliantly tuneful dissection of sexual politics from the point of view of both genders. The song debuted at #1 on the Billboard Hot 100. It also went to the top of the rap singles chart. Lauryn Hill won Grammy Awards for Best R&B Song and Best R&B Female Vocal Performance with "Doo Wop (That Thing)."

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07
of 10

4. Ricky Martin - "Livin' La Vida Loca"

Ricky Martin Livin' La Vida Loca
Ricky Martin - "Livin' La Vida Loca". Courtesy Columbia

Among Latin audiences, Ricky Martin was a household name by 1999 having begun his career many years before as a lead singer with the legendary teen group Menudo. With "Livin' La Vida Loca" the English-speaking world found out what they had been missing. It's irresistibly sexy and nearly impossible to listen to without moving the body. A performance of the song "La Copa De La Vida" at the Grammy Awards ceremony early in 1999 helped pave the way for this hit. The #1 pop chart success of "Livin' La Vida Loca" is seen by many as paving the way for later Latin pop artists such as Enrique Iglesias and Shakira.

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08
of 10

3. Cher - "Believe"

Cher Believe
Cher - "Believe". Courtesy Warner Bros.

No one really doubted Cher would eventually make another comeback, but this time it was with the biggest hit of her entire career. "Believe" is a perfect piece of dance-pop, and it took the entire world by storm. More dance hits followed in its wake and a farewell concert tour that lasted more than three years. The song's liberal use of auto-tune sound effects laid a controversial foundation for major pop hits to come. "Believe" was a #1 pop smash in most countries around the world and also topped the US dance chart.

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09
of 10

2. Santana - "Smooth" featuring Rob Thomas

Santana Smooth
Santana - "Smooth" featuring Rob Thomas. Courtesy Arista

"Smooth" genuinely appeared out of left field. Who would have thought legendary Latin guitarist Carlos Santana would record one of the biggest pop hit singles of all time? Add to that - who would have thought the vocalist would be the lead singer for post-grunge band Matchbox Twenty? It did happen and "Smooth" deserved the sales and acclaim. In 2005 Rob Thomas, the lead vocalist with Matchbox 20, proved his performance on "Smooth" was no fluke with a hit solo album ...Something To Be. "Smooth" spent a phenomenal twelve weeks at #1 on the US pop chart. It also earned three Grammy Awards including Record and Song of the Year. 

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10
of 10

1. Britney Spears - "...Baby One More Time"

Britney Spears Baby One More Time
Britney Spears - "...Baby One More Time". Courtesy Jive

Britney Spears first gained national notice as a member of The New Mickey Mouse Club on Disney's cable network, but it was as a pop singer that Britney Spears became the most watched celebrity in the world. Her first single "...Baby One More Time" is a brilliant piece of pop music. It's catchy, sexy, and it sports a mildly controversial video certain to keep people talking. The song was also one of the first international pop hits for writer and producer Max Martin. "...Baby One More Time" hit #1 on pop charts in most countries around the world.

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