75 Pictures That Perfectly Capture 1999

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

Table of Contents

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 / Getty Images

2.

Freddie Prinze Jr. with a large tie and suspenders.


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.


Fred Prouser / Getty Images

4.

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


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.

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.


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.


Dave Hogan / Getty Images

12.

Britney and NSYNC having a cute moment.

13.

The most important 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 some sort of clown at the VMAs.


Frank Micelotta Archive / Getty Images

15.

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

16.

This picture from the Election red carpet.


Reuters

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

17.

This picture from the She’s All That red carpet.

18.

A grown man with a Furby on his shoulder.

19.

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

20.

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

21.

Snoop Dogg making out with Kathy Griffin.

22.

NSYNC wearing reflective tape attached to all-leather outfits.

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.

25.

Shania Twain performing “Man! I Feel Like a Woman” at the Grammys.

26.

Brandy and Monica winning a Grammy for “The Boy Is Mine.”

27.

This random picture of Missy Elliott and Faith Hill.

28.

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

29.

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

30.

Jonathan Taylor Thomas just, like, existing.

31.

Iconic Kids Choice Awards host Rosie O’Donnell hosting the Kids Choice Awards.

32.

TLC wearing literal “T,” “L,” and “C.”

33.

Ricky Martin kissing Catherine Zeta-Jones.

34.

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

35.

Gender-bending legendary queen.

36.

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

37.

The Olsen Twins wearing scarves as skirts.


Jim Smeal / Ron Galella Collection via Getty Images

38.

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


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.


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.


Lucy Nicholson / AFP via Getty Images

44.

Ellen DeGeneres and Anne Heche in happier times.


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.


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.


Jeff Kravitz / FilmMagic, Inc / Getty Images

52.

Gwen Stefani in her braces era.


Evan Agostini / Getty Images

53.

The Sprouse twins barely fitting on some chairs.


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.”


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.


Dave Hogan / Getty Images

59.

Posh and Wax Posh — like, literally who is who?


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.


Albert L. Ortega / WireImage / Getty Images

62.

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


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.


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.


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.

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.


Ronald Siemoneit / Sygma via Getty Images

74.

Britney Spears looking very 2021 in 1999.


Chris Bacon / PA Images via Getty Images

75.

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

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