Celine Dion’s backward suit, very large ties, and more.
All of the following were taken in 1999…
Sandra Bullock and Matthew McConaughey as a couple, like I completely forgot they ever dated.
Freddie Prinze Jr. with a large tie and suspenders.
Freddie Prinze Jr. with his large tie and suspenders accepting “Hottie of the Year” at the Teen Choice Awards with fellow hottie winner, Jennifer Love Hewitt.
The members of Blink-182 getting intimate on a red carpet.
Kirsten Dunst and Michelle Williams filming one of the best comedies/movies of all time, Dick.
98 Degrees performing at a YM magazine party at some random Macy’s.
NSYNC in incredibly large, shiny, and puffy jackets.
Aaron Carter in a Hoku/JC Chasez sandwich.
This tween’s room.
Britney Spears having a casual conversation with Ricky Martin.
Britney Spears wearing a tiny jacket with her mouth wide open and eyes slightly crossed.
Britney and NSYNC having a cute moment.
The first couple of 1999, Jennifer Love Hewitt and Carson Daly.
Tommy Lee in his trench coat and Pamela Anderson dressed as a clown at the VMAs.
Ryan Phillippe and Reese Witherspoon on the Cruel Intentions red carpet.
This picture from the Election red carpet.
This picture from the She’s All That red carpet.
A grown man with a Furby on his shoulder.
Tom Hanks with a rare beard.
Fergie when she was part of the wildly successful girl group Wild Orchid.
Snoop Dogg making out with Kathy Griffin.
NSYNC wearing reflective tape attached to all-leather outfits.
AJ McClean being an early adopter of the male crop top.
Whitney and Mariah performing “When You Believe” at the Oscars.
Shania Twain performing “Man! I Feel Like a Woman” at the Grammys.
Brandy and Monica winning a Grammy for “The Boy Is Mine” before they hated each other.
This random picture of Missy Elliot and Faith Hill.
Ricky Martin and that iconic ribbed sweater thing he wore to the Grammys.
Married couple Tom Cruise and Nicole Kidman looking like straight-up wax figures.
Jonathan Taylor Thomas.
Iconic Kids Choice Awards host Rosie O’Donnell hosting the Kids Choice Awards.
TLC wearing literal “T,” “L,” and “C.”
Ricky Martin kissing Catherine Zeta-Jones.
Celine Dion in *the most* iconic Academy Awards look of all time.
Gender-bending legendary queen.
Ben Stiller and the dog, Puffy, from There’s Something About Mary.
And Hercules, the duck from Friends, walking the red carpet of the TV Guide Awards.
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