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

All of the following were taken in 1999...

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

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

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.

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

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.

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

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

9.This tween's room.

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

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

12.Britney and NSYNC having a cute moment.

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

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

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

16.This picture from the Election red carpet.

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.

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.

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

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

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

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

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

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

44.Ellen DeGeneres and Anne Heche in happier times.

45.Jen determined to get Brad Pitt home.

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

47.Brad and Jen at the Fight Club premiere.

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

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

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

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

52.Gwen Stefani in her braces era.

53.The Sprouse twins barely fitting on some chairs.

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

55.Adam Sandler originating the "Karen."

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

57.Charlize Theron and her teeny tiny bangs.

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

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

60.The Spice Girls when they were a foursome.

61.Britney Spears in her Greta Thunberg era.

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

63.The legendary Jessie Camp.

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

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

66.Sarah Jessica Parker and Derek Jeter getting close.

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

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

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

70.Elian Gonzalez opening a Nintendo 64 at Christmas.

71.Jennifer Lopez in her Puff Daddy era.

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

73.David Bowie and Iman.

74.Britney Spears looking very 2021 in 1999.

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