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    58 Pictures That Show How Messy, Weird, And Iconic The Years 1999 And 2000 Were

    The peak of pop culture.

    All of the following pictures were taken in 1999 and 2000.

    1. Steve Jobs holding up the Holy Bible.

    Steve Jobs holding up Britney Spears album Baby One More Time
    John G. Mabanglo / Getty Images

    2. Sisqo aggressively holding onto a thong like it's going to save his life or something.

    Chris Weeks / Getty Images

    3. Sandra Bullock and Matthew McConaughey when they were a couple. So weird!

    Steve Granitz / WireImage / Getty Images

    4. Destiny's Child with four members one month.

    Brenda Chase / Getty Images

    5. Destiny's Child with three members the next month.

    Nick Elgar / Getty Images

    6. The Spice Girls as a quartet.

    the spice girls with 4 members
    John Stillwell - Pa Images / Getty Images

    7. A.J. in his awkward phase.

    AJ standing in the middle in white
    Jim Smeal / Ron Galella Collection via Getty

    8. Baby Jake Gyllenhaal.

    he's so young
    Ron Galella / Ron Galella Collection via Getty

    9. Verne Troyer living his 1999 fantasy.

    verne in leather pants and baby sunglasses
    Barry King / Getty Images

    10. Anna Nicole Smith in full glam arriving to her bankruptcy hearing.

    Jim Ruymen / Getty Images

    11. Christina Aguilera being creeped out by whatever is underneath Tommy Lee's trench coat.

    christina giving tommy lee a look
    Dave Allocca / The LIFE Picture Collection via Getty Images

    12. Steve Jobs showing off his chunky Mac.

    Ted Thai / The LIFE Picture Collection via Getty Images

    13. Tom copping a feel.

    tom grabbing mark's chesticles
    Ron Galella / Ron Galella Collection via Getty Images

    14. 98 Degrees performing at some Macy's for a YM magazine launch party.

    Diane Freed / Getty Images

    15. NSYNC wearing large ski suits on some red carpet in LA.

    Steve Granitz / WireImage / Getty Images

    16. Britney Spears being cute.

    Britney with her eyes wide open
    Dave Hogan / Getty Images

    17. Freddie Prinze Jr. with a large tie and suspenders.

    Ron Galella, Ltd. / Ron Galella Collection via Getty Images

    18. Halle Berry proudly showing off her whale tail.

    Kevin Winter / Getty Images

    19. The fake but also real boy band, 2Gether.

    George De Sota / Getty Images

    Forever RIP QT.

    20. Pink with a huge chunk taken out of her pants.

    George De Sota / Getty Images

    How...do these work?

    how do the pants stay up they are barely hanging on
    George De Sota / Getty Images

    21. Tom Hanks sporting a Castaway beard.

    Reuters Photographer / Reuters

    22. NSYNC dressed from a high school drama club's costume chest.

    nsync in clothes that don't match at all
    Nick Elgar / Getty Images

    23. Christina Aguilera with clothing that is entirely tied on.

    Vince Bucci / Getty Images

    24. Wickedly talented and wildly successful girl group, Wild Orchid. Yes, that's Fergie.

    wild orchid showing their hands off
    Reuters Photographer / Reuters

    25. Snoop Dogg and Kathy Griffin making out.

    Reuters Photographer / Reuters

    26. Aaliyah being iconic.

    she's pointing at something
    Chris Weeks / Getty Images

    27. The only Charlie's Angels we acknowledge.

    lucy liu, drew barrymore, and cameron diaz
    Lucy Nicholson / Getty Images

    28. Britney Spears dressed as... I don't even know.

    britney in a weird orange outfit
    Chris Weeks / Getty Images

    29. Two of the greatest vocalists of all time sharing a stage.

    mariah carey and whitney houston singing together
    Gary Hershorn / Reuters

    30. Brandy and Monica winning a Grammy for "The Boy Is Mine."

    Reuters Photographer / Reuters

    31. Jennifer Lopez in *the dress.*

    the green dress
    Vince Bucci / Getty Images

    32. The South Park creators dressed as Jennifer Lopez in the dress.

    Scott Nelson / Getty Images

    33. Nicole Kidman and Tom Cruise looking very much like wax figures of themselves.

    Reuters Photographer / Reuters

    34. Lil' Kim's exposed boob.

    Brenda Chase / Getty Images

    35. Tom Green resting his head on a coffee maker on a red carpet.

    Lucy Nicholson / Getty Images

    36. Eve getting overly excited about writing an email in the TRL studios.

    Scott Gries / Getty Images

    37. Nick Lachey and Jessica Simpson when they pretended to like each other*.

    they're kissing
    Chris Weeks / Getty Images

    *I say this because I recently re-watched Newlyweds and they DID NOT get along.

    38. Mary-Kate and Ashley Olsen at the launch of their Game Boy game.

    full denim skirts
    Getty Images

    39. These two.

    Freddie Prinze Jr. and Sarah Jessica Parker
    Kmazur / WireImage

    40. A.J. McClean's facial hair.

    it's very carved
    Peter Carrette Archive / Getty Images

    41. Al Gore making out with his wife, Tipper.

    Mike Nelson / Getty Images

    Fun fact: They're divorced now!

    42. Jessica Simpson with feather arm bands.

    Chris Weeks / Getty Images

    43. Just, like, these tweens screaming while holding disposable cameras.

    Chris Hondros / Getty Images

    44. Tween rapping royalty, Lil' Bow Wow and Aaron Carter.

    Kevin Winter / Getty Images

    45. Angelina Jolie proudly showing off her Billy Bob tattoo.

    Lucy Nicholson / Getty Images

    That was a great idea!

    a closeup of the billy bob tattoo
    Lucy Nicholson / Getty Images

    46. Victoria and David Beckham meeting the Prince of Wales.

    Matthew Fearn / Getty Images

    47. Brad, his sunglasses, and Jen.

    Dan Callister / Getty Images

    48. A group of grown adults watching robot dogs playing robot dog soccer.

    Robert Cianflone / Getty Images

    49. Though I swear no one actually owned one of these at the time.

    the robot dogs
    Robert Cianflone / Getty Images

    50. NSYNC being lowered down from the ceiling dressed as human-sized marionettes.

    Getty Images

    51. JC Chasez and Joey Fatone in large, colorful furry coats touching a painting of a woman wearing a thong.

    Kevin Winter / Getty Images

    52. Brad and Jen looking pretty much exactly like they do today except obviously they aren't together anymore.

    Sam Levi / WireImage / Getty Images

    53. Celine Dion's iconic backwards tuxedo dress.

    Kmazur / WireImage / Getty Images

    54. Madonna smushing her face on Gwyneth Paltrow.

    Dave Allocca / The LIFE Picture Collection via Getty Images

    55. Britney Spears with shopping bags full of stuffed animals.

    Larry Marano / Getty Images

    56. These people dividing up their Beanie Baby collection as part of a divorce settlement.

    Aaron Mayes / Reuters

    57. And last but not least, Dwayne "The Rock" Johnson at the VMAs.

    the rock wearing gold latex clothing with an exposed chest
    Nick Elgar / Getty Images

    58. Mmm yeah.

    a closeup of the rock
    George De Sota / Getty Images

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