And now, fourteen years later, the singer has recreated her iconic look once more – with even more leg on show.
The 44-year-old (yes, that's right, 44) showed up to the Billboard Music Awards in Las Vegas last night in little more than undies and a cape.
Wearing a belted chiffon cape dress by Donna Karan, Jennifer's neckline plunged to her waist while the skirt of the frock was slashed up to her belly-button.
Just a pair of high-waisted knickers made this outfit acceptable for daylight, with every inch of the Get Right singer's pins on show.
As well as swapping a green tropical print for crimson chiffon, Jenny from the block also switched up her date.
The American Idol judge walked the red carpet at the MGM Grand with her toyboy fella Casper Smart, who dutifully rearranged Jen's skirt to avoid any embarrassing trips – all while sneaking a peek at her curves, natch.
Jennifer wasn't just at the Billboard awards to make us all feel inadequate though.
The sometimes actress became the first ever female recipient of the Icon Award, and also took to the stage to perform the official World Cup song with Pitbull and Claudia Leitte.
Following in the footsteps of Shakira, the trio of Latin stars were bestowed the honour of recording the official single for this summer's World Cup tournament in Rio, Brazil.
The video for We Are One (Ole Ola) was released this weekend, and has already achieved over 11 million views on YouTube.
As well as showing Miss Lopez gyrating in teeny shorts, the video is interspersed with carnival dancers in Rio and clips of players including Wayne Rooney and Steven Gerrard doing their thing on the pitch.
Something for everyone, then.
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