1. Ja Rule and Nelly posing with an iMac at the Sprite.com website launch party.

Scott Gries / Getty Images
2. Sisqo being petted by Tom Green holding a coffee machine.

Kevin Winter / Getty Images
3. Sisqo enthusiastically holding a Sisqo branded thong with purple-tinted sunglasses.

Chris Weeks / Getty Images
4. Farrah Franklin trying to get her five seconds of airtime talking to Rebecca Romijn-Stamos at MTV's Spring Break covered in denim while Beyoncé just stares like...

Frank Micelotta / Getty Images
5. ...

Frank Micelotta / Getty Images
6. And Michelle's like...

Frank Micelotta / Getty Images
7. Billy Ray Cyrus + soul patch and earring cuddles up on his daughter Miley.

Paul Hawthorne / Getty Images
8. Here's another, this time with Billy's chunky highlights and sunglasses.

Frazer Harrison / Getty Images
9. Brandy, Lil Kim, Ray J, and a mustachioed Pharrell on the set of "Wait A Minute."

Kevin Winter / Getty Images
10. Hilary Duff and Aaron Carter sharing a ~tender moment~ on the red carpet of The Lizzie McGuire Movie.

Lucy Nicholson / Getty Images
11. Ashton Kutcher, wearing a trucker hat, about to kiss Brittany Murphy.

Scott Gries / Getty Images
12. Jennifer Lopez staring at Justin Timberlake and Halle Berry in the TRL studios.

Frank Micelotta / Getty Images
13. A shirtless Fat Joe cuddles a very uncomfortable Ashanti.

Frank Micelotta / Getty Images
14. Eminem and "Dirrty" Christina being awkward.

Scott Gries / Getty Images
15. A very tanned Ryan Seacrest stands with a red Simon Cowell and a chunky-highlighted Kelly Clarkson.

Frank Micelotta / Getty Images
16. Jimmy Fallon wears a big fake mole while imitating Enrique Iglesias at the VMAs.

Frank Micelotta / Getty Images
17. A Band-Aid-wearing Nelly shakes hands with Justin Timberlake in a Coors Light shirt, large velvety hat, and a loose "Avril-esque" tie.

Matthew Peyton / Getty Images
18. Avril Lavigne and a pre-Fashion Police Kelly Osbourne perfecting the faux-punk trend of the early '00s.

Evan Agostini / Getty Images
19. Beyoncé, Carson Daly, and Mike Meyers promote Austin Powers 3 in the TRL studios.

Frank Micelotta / Getty Images
20. Freddie Prinze Jr. with some super-cute orange + oval sunglasses.

Frederick M. Brown / Getty Images
21. Tantina.

Getty Images
22. Tantina, this time with her signature leather chaps.

Frank Micelotta / Getty Images
23. Jessica Simpson being presented a shitload of tuna.

Sandy Huffaker / Getty Images
24. Lil Jon, a crunk cup, Hilary Duff, and Jason Biggs.

Frank Micelotta / Getty Images
25. Lindsay Lohan with distressed, flared jeans.

Evan Agostini / Getty Images
26. Nick and Jessica before shit hit the fan.

Frank Micelotta / Getty Images
27. Nick Carter, Ashanti, and a giant Polaroid of both of them.

Scott Gries / Getty Images
28. A ribbed-sweatered Frankie Muniz awkwardly standing with Amanda Bynes.

Vince Bucci / Getty Images
29. Hugh Jackman with those sunglasses and THAT HAIR.

Frazer Harrison / Getty Images
30. The ladies marmalade.

Frank Micelotta / Getty Images
31. Justin Timberlake at work.

Scott Gries / Getty Images
32. Solange, Jessica Simpson, Eve, Nelly, Destiny's Child, Dream, AND 3LW (!!!!!!!!!!!!!!).

Scott Gries / Getty Images
33. Ryan Seacrest, that shirt, Paris Hilton, and that dress.

Frederick M. Brown / Getty Images
34. Halle Berry repping her Von Dutch shirt, purple-tinted sunglasses, and flared jeans.

Michael Buckner / Getty Images
35. Britney Spears and Verne Troyer.

Kevin Winter / Getty Images
36. Even Steven's, Shia Labeouf.

Frazer Harrison / Getty Images
37. This woman's face watching Nick Carter and Paris Hilton make out.

Jeffrey Mayer / WireImage
38. Paris Hilton and Nicole Richie in full-on denim.

David Klein / Getty Images
39. Aaron Paul!!!!!!!

SGranitz / WireImage
40. Ben Affleck and Jennifer Lopez leaving Blockbuster together after a long bout of video shopping in clear platform shoes.

Jeff Vinnick / Getty Images
41. Justin Timberlake and Carson Daly exchange numbers on their typing machines.

Frank Micelotta / Getty Images
42. Toni Braxton literally applauding how ridiculous J.C. Chasez looks.

Getty Images
43. Britney + Justin in all over their ethereal glory.

Kevin Winter / Getty Images
44. Kristin Cavallari showing off her Sidekick.

Michael Buckner / Getty Images
45. Steve Jobs showing John Mayer the new iPod Mini.

Justin Sullivan / Getty Images
46. Eminem and Mark McGrath on the Joe Dirt premiere red carpet.

Chris Weeks / Getty Images
47. Early Rihanna at a Teen People party.

Kevin Winter / Getty Images
48. A very innocent-looking Rihanna with a very innocent-looking Amanda Bynes.

Evan Agostini / Getty Images
49. More Frankie Muniz.

Frank Micelotta / Getty Images
50. Kelly Clarkson and a VERY adorable Brittany Murphy.

Frank Micelotta / Getty Images
51. A goldie-locked Brad Pitt and Jim Carrey.

Frank Micelotta / Getty Images
52. The cast of Lizzie McGuire in all their supreme glory.

Robert Mora / Getty Images
53. Shia LaBeouf, Amanda Bynes, and Raven-Symoné sharing the TRL stage.

Peter Kramer / Getty Images
54. Britney, just before her downfall, and Kevin Federline's mane.

Kevin Winter / Getty Images
55. BABY EMMA WATSON.

George De Sota / Getty Images
56. A slightly aged Emma Watson and Daniel Radcliffe.

Scott Gries / Getty Images
57. Zac Efron's hair and pants.

Evan Agostini / Getty Images
58. Pete Wentz and his hat at the Sidekick 3 party.

Getty Images
59. Everyone laughing at Pink's tiny hat.

Steve Finn / Getty Images
60. And lastly, here's the one person who personifies the era... This is Tom, the founder of Myspace.

Mark Mainz / Getty Images