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

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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
Diane Freed / Getty Images

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

  Steve Granitz / WireImage / Getty Images
Steve Granitz / WireImage / Getty Images

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

  Jeff Kravitz / FilmMagic, Inc / Getty Images
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
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
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.

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

Reuters

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
Reuters

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

  Reuters
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
Reuters

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

  Reuters
Reuters

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

  Jeff Christensen / Getty Images
Jeff Christensen / Getty Images

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

  Gary Hershorn / Reuters
Gary Hershorn / Reuters

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

  Gary Hershorn
Gary Hershorn

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

  Reuters
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
Sam Mircovich / Reuters

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

  Reuters
Reuters

30.Jonathan Taylor Thomas just, like, existing.

  Reuters
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
Reuters

33.Ricky Martin kissing Catherine Zeta-Jones.

  Reuters
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
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
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
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
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
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
Jim Smeal / Ron Galella Collection via Getty Images

47.Brad and Jen at the Fight Club premiere.

  Jeff Kravitz / FilmMagic / Getty Images
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
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
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
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
Ron Galella, Ltd. / Ron Galella Collection via Getty Images

57.Charlize Theron and her teeny tiny bangs.

  Steve Granitz / WireImage / Getty Images
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 — 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
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
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
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
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
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
Pymca / Universal Images Group via Getty Images

70.Elian Gonzalez opening a Nintendo 64 at Christmas.

  AFP via Getty Images
AFP via Getty Images

71.Jennifer Lopez in her Puff Daddy era.

  Ron Galella / Ron Galella Collection via Getty Images
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
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