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    Updated on Aug 6, 2020. Posted on Aug 4, 2020

    37 Pictures That Show How Weird, Random, And Wonderful The Year 1999 Was

    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.

    Steve Granitz / WireImage

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

    Ron Galella, Ltd. / Ron Galella Collection via Getty

    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.

    Fred Prouser

    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

    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

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

    Jeff Kravitz / FilmMagic, Inc

    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

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

    Jeff Kravitz / FilmMagic, Inc

    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

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

    Dan Callister / Getty Images

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

    Frank Micelotta Archive / Getty Images

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

    Reuters Photographer

    16. This picture from the Election red carpet.

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

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

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

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

    Reuters Photographer / Reuters

    19. Tom Hanks with a rare beard.

    Reuters Photographer / Reuters

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

    Wild Orchid with their hands extended
    Reuters Photographer / Reuters

    21. Snoop Dogg making out with Kathy Griffin.

    Reuters Photographer / Reuters

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

    Reuters Photographer / Reuters

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

    Jeff Christensen

    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" before they hated each other.

    Reuters Photographer / Reuters

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

    Missy and Faith with some random guy
    Reuters Photographer / Reuters

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

    Sam Mircovich

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

    Reuters Photographer / Reuters

    30. Jonathan Taylor Thomas.

    Reuters Photographer / Reuters

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

    Rosie Odonnel with a guitar
    Reuters Photographer / Reuters

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

    Reuters Photographer / Reuters


    33. Ricky Martin kissing Catherine Zeta-Jones.

    Reuters Photographer / Reuters

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

    Celine Dion wearing a tuxedo backward
    Reuters Photographer / 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 Photographer / Reuters

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

    A duck with a bow tie
    Reuters Photographer / Reuters

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