3.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.
4.The members of Blink-182 getting intimate on a red carpet.
5.Kirsten Dunst and Michelle Williams filming one of the best comedies/movies of all time, Dick.
6.98 Degrees performing at a YM magazine party at some random Macy's.
7.NSYNC in incredibly large, shiny, and puffy jackets.
8.Aaron Carter in a Hoku/JC Chasez sandwich.
9.This tween's room.
10.Britney Spears having a casual conversation with Ricky Martin.
11.Britney Spears wearing a tiny jacket with her mouth wide open and eyes slightly crossed.
12.Britney and NSYNC having a cute moment.
13.The most important couple of 1999, Jennifer Love Hewitt and Carson Daly.
14.Tommy Lee in his trench coat and Pamela Anderson dressed as some sort of clown at the VMAs.
15.Ryan Phillippe and Reese Witherspoon on the Cruel Intentions red carpet.
16.This picture from the Election red carpet.
17.This picture from the She's All That red carpet.
18.A grown man with a Furby on his shoulder.
19.Tom Hanks with a beard, probably because he just filmed Cast Away.
20.Fergie when she was part of the wildly successful girl group Wild Orchid.
21.Snoop Dogg making out with Kathy Griffin.
22.NSYNC wearing reflective tape attached to all-leather outfits.
23.AJ McClean being an early adopter of the male crop top.
24.Whitney and Mariah performing "When You Believe" at the Oscars.
25.Shania Twain performing "Man! I Feel Like a Woman" at the Grammys.
26.Brandy and Monica winning a Grammy for "The Boy Is Mine."
27.This random picture of Missy Elliott and Faith Hill.
28.Ricky Martin and that iconic ribbed sweater thing he wore to the Grammys.
29.Married couple Tom Cruise and Nicole Kidman looking like straight-up wax figures.
