1. Jennifer Aniston sniffing Jake Gyllenhaal's neck. J. Vespa / WireImage / Getty Images
2. Ryan Reynolds kissing Alanis Morissette's hand in a weird way. Jeff Kravitz / FilmMagic / Getty Images
3. Like, these two were always kissing. Kevin Winter / Getty Images
4. Get a room!!!! Jeff Kravitz / FilmMagic / Getty Images
5. Madonna in her brief and incredibly random "children's book author" era. Frank Micelotta / Getty Images
6. Lance Bass and someone Getty Images refers to as "girlfriend Carrah." Dimitrios Kambouris / WireImage / Getty Images
7. Steve Jobs showing the world how to burn a CD. Kim Kulish / Corbis via Getty Images
8. Nick Lachey and Jessica Simpson posing with some off-brand MP3 players. Djamilla Rosa Cochran / WireImage / Getty Images
9. Ludacris illegally downloading songs off of Napster. Jeff Christensen / WireImage / Getty Images
10. Avril Lavigne in a wee ole top hat showing off the "Rock On" letters she put inside her coat with white electrical tape. Steve Granitz / WireImage / Getty Images
11. Lance Bass showing off his jean charms. Frazer Harrison / Getty Images
12. Seriously, this was a thing. Frazer Harrison / Getty Images
13. Leonardo DiCaprio kissing the cheek of a very enthusiastic Gisele Bündchen. Vince Bucci / Getty Images
14. Penn Badgley in his teenage dirtbag phase. Barry King / WireImage / Getty Images
15. Anna Nicole surrounded by a bunch of Anna Nicole drag queens. Steve Grayson / WireImage / Getty Images
16. Donald Trump and Melania when they were still invited to the Met Gala. Fairchild Archive / Penske Media via Getty Images
17. Mary-Kate and Ashley Olsen auditioning to be Charlie's newest angels. L. Cohen / WireImage / Getty Images
18. Britney Spears and Colin Farrell on that one date they went on. Kevin Winter / Getty Images
19. Tom Cruise prom posing with his then-girlfriend Penélope Cruz. Christopher Polk / FilmMagic / Getty Images
20. Pamela Anderson ignoring David Spade. Frank Micelotta / Getty Images
21. The singer-songwriter herself, Stacie Orrico. Theo Wargo / WireImage / Getty Images
22. Mandy Moore and Andy Roddick when they were briefly an item. Victor Baldizon / NBAE via Getty Images
23. Brittany Murphy caressing a Skechers sandal. J. Vespa / WireImage / Getty Images
24. Jennifer Coolidge when she was *just* Stifler's mom. Jon Kopaloff / FilmMagic / Getty Images
25. Britney Spears hearing the latest rumor about herself. Scott Gries / Getty Images
26. T.A.T.u. pretending to be lesbians. Kmazur / WireImage / Getty Images
27. Christina Aguilera dressed as a very tan nun. Getty Images
28. Paul Rudd taking pictures with a very tiny cellphone. J. Vespa / WireImage / Getty Images
29. That phone was very tiny!! J. Vespa / WireImage / Getty Images
30. Nelly wearing a Band-Aid as fashion. Steve Granitz / WireImage / Getty Images
31. Ashlee Simpson in her extremely 2003 knitted beanie cap, and Frankie Muniz in his extremely 2003 Urban Outfitters graphic T-shirt. Christopher Polk / FilmMagic / Getty Images
32. Michelle Branch showing off her Maxim cover. Dimitrios Kambouris / WireImage for Maxim / Getty Images
33. Joe Rogan showing pictures on his digital camera to some cocktail servers at the "Warm and Fuzzy" Maxim party. Kevin Winter / Getty Images
34. Ben Affleck's chin strap. Ezra Shaw / Getty Images
35. Ben Affleck leaving a Blockbuster mid-argument. Jeff Vinnick / Getty Images
36. David Beckham with cornrows. Ben Radford / Getty Images
37. A distraught Claymate waiting for her dream man. Jon Gardiner / Getty Images
38. Pretend millionaire "Joe Millionaire" at the Just Married movie premiere. Gregg Deguire / WireImage / Getty Images
39. Beyoncé discovering the 9/11 tapes. Kmazur / WireImage / Getty Images
40. Two very angry Hot Topic employees. Evan Agostini / Getty Images
41. Britney Spears and Madonna showing off their friendship necklaces. Kmazur / WireImage / Getty Images
42. Lindsay Lohan showing off her new cellphone. Djamilla Rosa Cochran / WireImage / Getty Images
43. Many, many Beyoncés. Kmazur / WireImage / Getty Images
44. Pink making a man sniff her crotch. Kevin Winter / Getty Images
45. Then–New York City mayor Michael Bloomberg campaigning for Clay Aiken. Myrna Suarez / Getty Images
46. Jessica Simpson taking a picture with a very large basket of tuna. Sandy Huffaker / Getty Images
47. Fergie in some very interesting, extremely low-rise puff pants. Stephen Lovekin / FilmMagic / Getty Images
48. Nick Cannon in his beefcake era. Bob Berg / Getty Images
49. A not-staged-at-all photo of Prince William playing golf on the beach. Pool / Tim Graham Photo Library via Getty Images
50. Prince William giving away feet pics for free. Tim Graham / Corbis via Getty Images
51. Prince Harry in his dorm room. Pool / Tim Graham Photo Library via Getty Images
52. Prince Harry casually making toast while wearing a suit. Pool / Tim Graham Photo Library via Getty Images
53. Beyoncé and Ashton Kutcher joshing around. Jeff Kravitz / FilmMagic / Getty Images
54. Demi Moore and Ashton Kutcher as a couple. James Devaney / WireImage / Getty Images
55. Ashton Kutcher briefly becoming a member of the Willis-Moore family. L. Cohen / WireImage / Getty Images
56. Cameron Diaz and Drew Barrymore walking to the Charlie's Angels premiere after their limo broke down. Tom Wargacki / WireImage / Getty Images
57. Hilary Duff in her dating Aaron Carter era. L. Cohen / WireImage / Getty Images
58. Ryan Seacrest serving FASHION. Christopher Polk / FilmMagic / Getty Images
59. Work, bitch! Albert L. Ortega / WireImage / Getty Images
60. And last but not least, Dolly Parton posing with a tube of toothpaste so she could get it for free. Frazer Harrison / Getty Images
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