All of the following pictures were taken in 1999 and 2000.
Steve Jobs holding up the Holy Bible.
Sisqo aggressively holding onto a thong like it’s going to save his life or something.
Sandra Bullock and Matthew McConaughey when they were a couple. So weird!
Destiny’s Child with four members one month.
Destiny’s Child with three members the next month.
The Spice Girls as a quartet.
A.J. in his awkward phase.
Baby Jake Gyllenhaal.
Verne Troyer living his 1999 fantasy.
Anna Nicole Smith in full glam arriving to her bankruptcy hearing.
Christina Aguilera being creeped out by whatever is underneath Tommy Lee’s trench coat.
Steve Jobs showing off his chunky Mac.
Tom copping a feel.
98 Degrees performing at some Macy’s for a YM magazine launch party.
NSYNC wearing large ski suits on some red carpet in LA.
Britney Spears being cute.
Freddie Prinze Jr. with a large tie and suspenders.
Halle Berry proudly showing off her whale tail.
The fake but also real boy band, 2Gether.
Pink with a huge chunk taken out of her pants.
How…do these work?
Tom Hanks sporting a Castaway beard.
NSYNC dressed from a high school drama club’s costume chest.
Christina Aguilera with clothing that is entirely tied on.
Wickedly talented and wildly successful girl group, Wild Orchid. Yes, that’s Fergie.
Snoop Dogg and Kathy Griffin making out.
Aaliyah being iconic.
The only Charlie’s Angels we acknowledge.
Britney Spears dressed as… I don’t even know.
Two of the greatest vocalists of all time sharing a stage.
Brandy and Monica winning a Grammy for “The Boy Is Mine.”
Jennifer Lopez in *the dress.*
The South Park creators dressed as Jennifer Lopez in the dress.
Nicole Kidman and Tom Cruise looking very much like wax figures of themselves.
Lil’ Kim’s exposed boob.
Tom Green resting his head on a coffee maker on a red carpet.
Eve getting overly excited about writing an email in the TRL studios.
Nick Lachey and Jessica Simpson when they pretended to like each other*.
Mary-Kate and Ashley Olsen at the launch of their Game Boy game.
A.J. McClean’s facial hair.
Al Gore making out with his wife, Tipper.
Jessica Simpson with feather arm bands.
Just, like, these tweens screaming while holding disposable cameras.
Tween rapping royalty, Lil’ Bow Wow and Aaron Carter.
Angelina Jolie proudly showing off her Billy Bob tattoo.
That was a great idea!
Victoria and David Beckham meeting the Prince of Wales.
Brad, his sunglasses, and Jen.
A group of grown adults watching robot dogs playing robot dog soccer.
Though I swear no one actually owned one of these at the time.
NSYNC being lowered down from the ceiling dressed as human-sized marionettes.
JC Chasez and Joey Fatone in large, colorful furry coats touching a painting of a woman wearing a thong.
Brad and Jen looking pretty much exactly like they do today except obviously they aren’t together anymore.
Celine Dion’s iconic backwards tuxedo dress.
Madonna smushing her face on Gwyneth Paltrow.
Britney Spears with shopping bags full of stuffed animals.
These people dividing up their Beanie Baby collection as part of a divorce settlement.
And last but not least, Dwayne “The Rock” Johnson at the VMAs.
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