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Our frivolous yet rigorous investigation has revealed that 1999 was a treasure trove for some of pop music’s biggest hits. In fact, eight of our favourite songs of all time will turn 20 this year. As of right now, think pieces about Britney Spears’ ‘…Baby One More Time’ are sweeping the internet. The seminal album came out two decades ago on January 12, which is blowing some people’s minds. But ‘BOMT’ wasn’t unique in its timing. So we decided to quiz ourselves on some of the evergreen chart-toppers that came out in 1999. How many can you guess?

Song 1: An iconic American girl group went to No 1 for the third time with this single. The song is about a man who doesn’t have his own car — or, presumably, his own money — but is still trying to get with the girl, who doesn’t want him back. The second-biggest Hot 100 single of 1999 in America, it was bested only by Cher’s ‘Believe’. And it makes for the perfect karaoke pick every time. Can you guess it?

Song 2: It’s hard to believe this song came from a certain Latin pop star’s self-titled debut album, rather than his second or third. It’s typically credited as a song that launched Latin pop music into the international mainstream, and it encouraged other Spanish-singing artists like Enrique Iglesias and Shakira to break into foreign markets, too. This crazy track is one of the best-selling singles of all time — and it’s the singer’s biggest hit to date.

Song 3: It’s considered this American boy band’s most recognisable single to date, hitting No 1 in more than 25 countries. Despite how catchy it is, the lyrics are nonsensical — something that the band itself admitted. In fact, the original version of the song, penned by pop genius Max Martin, was re-written to make more sense, but the band rejected the alternate version, opting to go for the first one instead. If you still haven’t guessed it — the music video was filmed in an airport, which was equally mind-boggling at the time.

Song 4: This track was a massive hit from the soundtrack of a steampunk-western-action-comedy film. How’s that for a mouthful? The man who sung it — or rather, rapped it — is primarily known for being an actor, and was one of the lead actors of the movie that the song was featured on. The fresh track samples Stevie Wonder’s 1976 hit ‘I Wish’, and features Kool Moe Dee’s vocals in the chorus. What could it be?

Song 5: This was the debut single by a widely beloved Puerto Rican music artist from New York — you may have recently spotted her on the big screen in a new film with her BFF, actress Leah Remini. Co-written by pop-R’n’B hit-maker Rodney Jerkins, the track explores all the possibilities of what would happen if our protagonist let her suitor into her heart. It was the first of many No 1’s to come for this sensational pop star.

Song 6: Sung in both English and Spanish, this song with a single-word title that means ‘We Dance’ has been praised for making Latin pop more accessible to a global audience. It was also featured on the same soundtrack from Song 4. Sung by a chiselled pop star who has a defining facial mark, this track was written and produced by the same team behind Cher’s hit ‘Believe’. It was this singer’s debut single in the English-language market, released on his self-titled English album.

Song 7: She was painted as Britney Spears’ biggest competitor, but time has proven there’s more than enough room for both of these 90s pop divas. This slyly sensual track — the lead single off of her self-titled debut album — might make you think involuntarily of Aladdin and his three wishes. It topped the charts in more than 20 countries and is still considered this pop star’s signature song.

Song 8: This collaboration between a Latin band (named after their iconic guitarist) and the lead singer of an American rock group was unstoppable when it came out. Without hitting a single rough patch (hint hint), it won three Grammy Awards — Record of the Year, Song of the Year, and Best Pop Collaboration with Vocals. As of right now, it’s considered the second most successful song ever by Billboard.

Answers: Song 1: TLC – No Scrubs (February 2, 1999), Song 2: Ricky Martin - Livin’ la Vida Loca (March 23, 1999), Song 3: Backstreet Boys – I Want It That Way (April 12, 1999), Song 4: Will Smith – Wild Wild West (May 4, 1999), Song 5: Jennifer Lopez – If You Had My Love (May 11, 1999), Song 6: Enrique Iglesias – Bailamos (June 15, 1999), Song 7: Christina Aguilera – Genie in a Bottle (June 22, 1999), Song 8: Santana ft Rob Thomas – Smooth (June 29, 1999)