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Emmys 2017
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Chart Flashback: 1999

It may not have delivered quite the party times that Prince predicted back in 1982, but the second week of September 1999 did bring some major pre-Y2K pop moments

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1. Enrique Iglesias, ”Bailamos”
America’s hombre caliente cup ranneth over in ’99: With the road to la vida Latin loca already paved by Ricky ”Sweet Hips” Martin, Enrique dropped this horn-heavy invitation to the dance floor, landing his first English-language smash. B+

2. TLC, ”Unpretty”
Way before Gaga, Katy, et al. made self-esteem anthems de rigueur, T-Boz, Left Eye, and Chilli offered their own excellent call to arms for girls emotionally shipwrecked by mean boys and beauty myths. A

3. LFO, ”Summer Girls”
”New Kids on the Block had a bunch of hits/Chinese food makes me sick”: Okay, so Lord Byron was not exactly quaking in his romance boots. But what the Lyte Funky Ones (epically) lacked in lyrical poetry, their ode to Abercrombie-wearing ladies made up for in pure boy-band fizz. B+

4. Christina Aguilera, ”Genie in a Bottle”
Soon enough, she’d be putting the X in Xtina; 12 years ago, though, Aguilera offered a still-sweet tease of teen longing. A-

5. Garth Brooks As Chris Gaines, ”Lost in You”
Remember when Garth ditched his Stetson for a sop-rock alter ego with a soul patch? No? Lucky. C

6. Santana Feat. Rob Thomas, ”Smooth”
One honking dose of gimme-your-heart-make-it-real-or-else-foegettaboutit, and ”that ’60s guitar guy” and ”the dude from Matchbox Twenty” became chart demigods — holding down 12 weeks at No. 1 and snagging three Grammys. B+

7. Smash Mouth, ”All Star”
The amiable house band for bros in rayon bowling shirts and wraparound shades (raise your hand, Guy Fieri) scored big with their inescapable tailgate anthem. B-

8. 702, ”Where My Girls At?”
Like many ’90s R&B girl groups, this Las Vegas trio would soon be lost to the sands of time, but their hands-off-my-man directive still sways, from the front to back. B+

9. Destiny’s Child, ”Bills, Bills,Bills”
Time — and trifling, fake-baller boyfriends who can’t pay their own ”automo’bills” — were no match for the already-proto Sasha Fierce & Co. A-

10. Sugar Ray, ”Someday”
The rayon-shirt bros needed a lot of songs on their pre-millennium playlist, okay? They had so many light beers to drink and tribal-tattoo sessions to regret later. B

Source: Joel Whitburn Presents The Billboard® Hot 100® Charts—The Nineties