Flashback: See Brad Pitt, Jennifer Aniston and More Stars at the 1999 Emmys

As far as award shows go, the 1999 Emmys was one of the most star-studded events of the year.

Not only did it see all of TV’s biggest stars turn out, but there were a ton of movie stars walking the carpet too. At the time, A-listers like Brad Pittand Julia Robertswere dating Jennifer Anistonand Benjamin Bratt, which made for some lovely photos. Then, there were the stars who were not yet known on the big screen, but were poised to make a huge splash with their roles over the years. For example, a bright-eyed and glamorous Michelle Williams walked the carpet solo in a lovely pink gown. 

In retrospect, 1999 was giving pop culture fans a preview of the many faces that would appear on our TV screens for years to come. Jennifer Aniston would leave the set of Friends to become a favorite in the rom-com genre, while the ladies of Sex and the City would later make an entire film franchise out of their popular series. 

Most of all, the red carpet at the Forum in 1999 offered a peek at the styles that people are once again wearing 20 years later. The small framed sunglasses and dainty purses are basically the same styles that are modeled today. 

But maybe, the biggest takeaway from the 1999 show is how loyal and devoted the stars’ fans are. After all, some of these same exact same shows were so beloved, fans basically demanded they be rebooted. 

To see just how much the 1999 show mirrors the present-day, check out the gallery here!

Watch E!’s Live From the Red Carpet: The 2019 Emmy Awards coverage, beginning with the Countdown special, Sunday, Sept. 22 starting at 4:30 p.m. ET/1:30 p.m. PT! And after the Emmys telecast, recap the night’s biggest moments by watching the E! After Party special at 11 p.m.! Monday, Sept. 23, don’t miss E! News at 7 p.m. for all things Emmys!

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