Top 100 Movies Of The 1990's: #17 Swingers

Box Office: $4.6 Million

Oscar Nominations: None

Oscar Wins: None

MovieRankings.Net: 91/100

Available To Stream: Amazon Prime ($$), MGM+, Paramount+

For a movie that was pretty cool when it came out, Swingers has stayed pretty timeless. It may be because the idea of everything these guys are doing longs for a different era. From the dancing, the clubs, the music and even how Vince Vaughn's character Trent approaches dating, these guys want to be in 1962. Because of that, the movie isn't stuck in a specific era. It's almost like a time travel movie in that way.

The other reason is because Jon Favreau's great script deals with pretty eternal things like dating, being young and not confident, trying to figure out what you want to do and dealing with breakups. This was relatable in 1996 and still relatable in 2024.

What Swingers is probably most known for now is how it put Favreau, Vaughn, Heather Graham and Ron Livingston on the map. Even the director Doug Liman, went on to do some pretty giants hits with Edge Of Tomorrow, Mr and Mrs. Smith and The Bourne Identity. Much like watching Freaks & Geeks, it's fun seeing so many talented people just starting out that is also very good.

Vince Vaughn as Trent leaps off the screen. He's immediately a movie star. You can see why Steven Spielberg then immediately cast him in the (lousy) Jurassic Park sequel The Lost World. Everyone in 1997 wanted to be in the Vince Vaughn business. He was also in one of the most needless movies every made: the Psycho shot-for-shot remake. Even though he burst on the scene as a funny guy in a comedy, it took four years for him to be in a comedy again. Then, unsurprisingly, his career finally really took off.

But this is Jon Favreau's movie. He wrote the script and is the only person on screen for 3 minutes of the most uncomfortable moment in comedy history:

I'm biased because I'm such a big Favreau fan. How many other guys can direct one of the most important superhero movies in Iron Man, a Christmas movie with Elf and also a tiny movie about a food trucks with Chef? Not only that, but all three are fantastic movies. He can act, write and direct. He did a small show on IFC at the beginning of the century called Dinner For Five where he would have four other guests on to (very) casually talk about movies and life. If you have a chance to catch some old episodes on YouTube, they are must watch.

This isn't a movie I love because the people involved became huge. I loved this movie the second I stepped out of the movie theater in 1996. I laugh and enjoy the movie just as much 28 years later. I'm just glad the people involved had great careers. When they make something this good, they deserve it.

17. Swingers

18. Reservoir Dogs

19. There's Something About Mary

20. Sleepers

21. Schindler's List

22. Rushmore

23. Fight Club

24. Saving Private Ryan

25. True Romance

26. Dumb & Dumber

27. Kingpin

28. Donnie Brasco

29. Heat 

30. Terminator 2: Judgement Day

31. Rounders

32. Unforgiven

33. Trainspotting

34. The Game

35. Out Of Sight

36. Carlito's Way

37. Seven

38. L.A. Confidential

39. Speed

40. Gattaca

41. Misery

42. Tombstone

43. Ransom

44. Wayne's World

45. The Insider

46. Back To The Future Part III

47. A Bronx Tale

48. The People Vs. Larry Flynt

49. Eyes Wide Shut

50. The Sandlot

51. Happy Gilmore

52. Contact

53. The Green Mile

54. Man On The Moon

55. Boyz N The Hood

56. Grosse Pointe Blank

57. Independence Day

58. The Rainmaker

59. Go

60. The Firm

61. Magnolia

62. The Talented Mr. Ripley

63. Tommy Boy

64. The Usual Suspects

65. In The Line Of Fire

66. My Cousin Vinny

67. Awakenings

68. JFK

69. Toy Story

70. Home Alone

71. Jerry Maguire

72. Titanic

73. Billy Madison

74. Apollo 13

75. Braveheart

76. Edward Scissorhands

77. Cape Fear

78. The River Wild

79. What's Eating Gilbert Grape?

80. 12 Monkeys

81. Stir Of Echoes

82. Mission: Impossible

83. Total Recall

84. Quiz Show

85. For Love Of The Game

86. Being John Malkovich

87. Men In Black

88. Scream

89. Alive

90. Three Kings

91. Glengarry Glen Ross

92. Die Hard With A Vengeance

93. The Blair Witch Project

94. Twister

95. Dirty Work

96. Election

97. Tremors

98. Any Given Sunday

99. The Wedding Singer

100. Clerks