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    75 Pictures From 1999 That Prove Once And For All It Was The Greatest And Strangest Year Ever

    Celine Dion's backward suit, very large ties, and more.

    All of the following were taken in 1999...

    1. Sandra Bullock and Matthew McConaughey as a couple. Like, I completely forgot they ever dated.

    at the teen choice awards
    Steve Granitz / WireImage / Getty Images

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

    at teen choice awards
    Ron Galella, Ltd. / Ron Galella Collection via Getty Images

    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.

    with jennifer love hewitt
    Fred Prouser / Getty Images

    4. The members of Blink-182 getting intimate on a red carpet.

    The members of Blink 182 feeling Mark Hoppus' chest
    Ron Galella / Ron Galella Collection via Getty Images

    5. Kirsten Dunst and Michelle Williams filming one of the best comedies/movies of all time, Dick.

    Kirsten Dunst and Michelle Williams in American flag clothing
    Getty Images

    6. 98 Degrees performing at a YM magazine party at some random Macy's.

    Diane Freed / Getty Images

    7. NSYNC in incredibly large, shiny, and puffy jackets.

    Steve Granitz / WireImage / Getty Images

    8. Aaron Carter in a Hoku/JC Chasez sandwich.

    Jeff Kravitz / FilmMagic, Inc / Getty Images

    9. This tween's room.

    A teenager in his room covered with posters of Britney Spears and Sarah Michelle Geller
    Pymca / Universal Images Group via Getty Images

    10. Britney Spears having a casual conversation with Ricky Martin.

    Jeff Kravitz / FilmMagic / Getty Images

    11. Britney Spears wearing a tiny jacket with her mouth wide open and eyes slightly crossed.

    Britney Spears with her mouth wide open
    Dave Hogan / Getty Images

    12. Britney and NSYNC having a cute moment.

    Britney and NSYNC sitting on steps smiling
    Kevin.mazur / WireImage / Getty Images

    13. The most important couple of 1999, Jennifer Love Hewitt and Carson Daly.

    at the vmas
    Dan Callister / Getty Images

    14. Tommy Lee in his trench coat and Pamela Anderson dressed as some sort of clown at the VMAs.

    Frank Micelotta Archive / Getty Images

    15. Ryan Phillippe and Reese Witherspoon on the Cruel Intentions red carpet.

    dressed casual cool
    Reuters

    16. This picture from the Election red carpet.

    Chris Klein, Reese Witherspoon, Matthew Broderick and Molly Hagan.
    Reuters

    Election is one of the most underrated movies of all time, btw.

    17. This picture from the She's All That red carpet.

    Anna Paquin, Freddie Prinze Jr., and Rachel Leigh Cook
    Reuters

    18. A grown man with a Furby on his shoulder.

    Reuters

    19. Tom Hanks with a beard, probably because he just filmed Cast Away.

    Reuters

    20. Fergie when she was part of the wildly successful girl group Wild Orchid.

    Wild Orchid with their hands extended
    Reuters

    21. Snoop Dogg making out with Kathy Griffin.

    Reuters

    22. NSYNC wearing reflective tape attached to all-leather outfits.

    Reuters

    23. AJ McClean being an early adopter of the male crop top.

    Jeff Christensen / Getty Images

    24. Whitney and Mariah performing "When You Believe" at the Oscars.

    Gary Hershorn / Reuters

    25. Shania Twain performing "Man! I Feel Like a Woman" at the Grammys.

    Gary Hershorn

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

    Reuters

    27. This random picture of Missy Elliott and Faith Hill.

    Missy and Faith with some random guy
    Reuters

    28. Ricky Martin and that iconic ribbed sweater thing he wore to the Grammys.

    Sam Mircovich / Reuters

    29. Married couple Tom Cruise and Nicole Kidman looking like straight-up wax figures.

    Reuters

    30. Jonathan Taylor Thomas just, like, existing.

    Reuters

    31. Iconic Kids Choice Awards host Rosie O'Donnell hosting the Kids Choice Awards.

    Rosie Odonnel with a guitar
    Reuters

    32. TLC wearing literal "T," "L," and "C."

    Reuters

    33. Ricky Martin kissing Catherine Zeta-Jones.

    Reuters

    34. Celine Dion in *the most* iconic Academy Awards look of all time.

    Celine Dion wearing a tuxedo backward
    Reuters

    35. Gender-bending legendary queen.

    Celine Dion in her backward tuxedo
    Getty Images

    36. Ben Stiller and the dog, Puffy, from There's Something About Mary.

    Reuters

    37. The Olsen Twins wearing scarves as skirts.

    ankle length skirts
    Jim Smeal / Ron Galella Collection via Getty Images

    38. Britney Spears and Joey McIntyre getting a convertible tour of Disney World.

    in a convertible
    James Devaney / WireImage / Getty Images

    39. Steve Jobs trying to make collecting large desktop computers happen.

    John G. Mabanglo / AFP via Getty Images

    40. Just, like, this picture of a mall with people *actually* shopping.

    the mall of america
    Carolyn Schaefer / Getty Images

    41. A bunch of people watching some robot dogs "play."

    Kurita Kaku / Gamma-Rapho via Getty Images

    42. Bruce Willis in a leather cap at a premiere for The Sixth Sense.

    Stephane Cardinale - Corbis / Sygma via Getty Images

    43. Verne Troyer, Robert Wagner, and Rob Lowe doing the Dr. Evil.

    they have their pinkies up to their mouths
    Lucy Nicholson / AFP via Getty Images

    44. Ellen DeGeneres and Anne Heche in happier times.

    at the academy awards
    Steve Granitz / WireImage / Getty Images

    45. Jen determined to get Brad Pitt home.

    Andrew Shawaf / Getty Images

    46. The cast of Friends at some award show before it was impossible to get them all in a room together.

    Jim Smeal / Ron Galella Collection via Getty Images

    47. Brad and Jen at the Fight Club premiere.

    Jeff Kravitz / FilmMagic / Getty Images

    48. Roseanne looking at a newspaper that says Bill Clinton was acquitted.

    on leno
    Nbc / NBCU Photo Bank/NBCUniversal via Getty Images

    49. Meryl Streep embracing Bill Clinton in a deep hug.

    Kmazur / WireImage / Getty Images

    50. Cher and Sarah Michelle Gellar at a press conference for Diva's Live.

    Ron Galella / Ron Galella Collection via Getty Images

    51. Freddie Prinze Jr. when he was dating someone who wasn't Sarah Michelle Gellar.

    at the teen choice awards
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    52. Gwen Stefani in her braces era.

    bright pink hair and braces
    Evan Agostini / Getty Images

    53. The Sprouse twins barely fitting on some chairs.

    on leno
    Nbc / NBCU Photo Bank/NBCUniversal via Getty Images

    54. The Sprouse twins and their babysitter, Adam Sandler.

    Jim Smeal / Ron Galella Collection via Getty Images

    55. Adam Sandler originating the "Karen."

    swoopy bangs
    Mario Magnani / Getty Images

    56. Edward Furlong and actress Natasha Lyonne sharing a cig on the American Pie red carpet.

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

    57. Charlize Theron and her teeny tiny bangs.

    Steve Granitz / WireImage / Getty Images

    58. Baby Spice reading fan mail on her 23rd birthday.

    she's holding up an angelica card
    Dave Hogan / Getty Images

    59. Posh and Wax Posh โ€” like, literally who is who?

    posh and her wax figure
    Adrian Dennis / AFP via Getty Images

    60. The Spice Girls when they were a foursome.

    John Stillwell - Pa Images / PA Images via Getty Images

    61. Britney Spears in her Greta Thunberg era.

    at the big help
    Albert L. Ortega / WireImage / Getty Images

    62. Macho Man Randy Savage making out with someone after being slimed at the Kids Choice Awards.

    lots of tongue
    Steve Granitz / WireImage / Getty Images

    63. The legendary Jessie Camp.

    Brenda Chase / Getty Images

    64. AJ McLean trying to stand out from the rest of the boys, but instead he looks kinda sad.

    theyre in all black and hes in white
    Fotos International / Getty Images

    65. Dennis Rodman and Carmen Electra at a Planet Hollywood.

    Steve W. Grayson / Getty Images

    66. Sarah Jessica Parker and Derek Jeter getting close.

    theyre touching at a macys event
    Ron Galella / Ron Galella Collection via Getty Images

    67. Some guy looking up Beanie Babies on the internet.

    Glenn Koenig / Los Angeles Times via Getty Images

    68. Nicole Kidman and Jason Biggs having a gay ol' time.

    Jeff Kravitz / FilmMagic, Inc / Getty Images

    69. A tween in a room covered with pictures he tore out from a magazine.

    Pymca / Universal Images Group via Getty Images

    70. Elian Gonzalez opening a Nintendo 64 at Christmas.

    AFP via Getty Images

    71. Jennifer Lopez in her Puff Daddy era.

    Ron Galella / Ron Galella Collection via Getty Images

    72. Limp Bizkit looking very proud of Ricky Martin for winning a VMA.

    Kmazur / WireImage / Getty Images

    73. David Bowie and Iman.

    at the vmas
    Ronald Siemoneit / Sygma via Getty Images

    74. Britney Spears looking very 2021 in 1999.

    tiny baby sunglasses and a bucket hat
    Chris Bacon / PA Images via Getty Images

    75. And Hercules, the duck from Friends, walking the red carpet of the TV Guide Awards.

    A duck with a bow tie
    Reuters

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