Top 100 Movies Of The 1990's: #4 Good Will Hunting

Box Office: $138.4 Million Dollars

Oscar Nominations: Best Picture, Best Director (Gus Van Sant), Best Actor (Matt Damon), Best Supporting Actor (Robin Williams), Best Supporting Actress (Minnie Driver), Best Original Screenplay, Best Film Editing, Best Score, Best Song

Oscar Wins: Best Supporting Actor (Robin Williams), Best Original Screenplay

MovieRankings.Net: 97/100

Available To Stream:  Pluto TV (On Showtime at 6:30 PM on Saturday)

No movie portrays male friendship better than Good Will Hunting. Good friends are there for you. But the best of friends care more about you than they care about the friendship. Best friends want you to live your greatest life possible. Having another human being care about you that much is rare. Having that person not even be related to you is priceless. If you can count people in your life like that on even one hand, consider yourself very lucky.

Will (Matt Damon) has that with Chuckie (Ben Affleck). Them actually being friends makes this feel so authentic. On the job site when Chuckie tells Will that he needs to have a better life isn't just one of my favorite scenes of the 1990's. It's one of my favorite scenes ever. Chuckie's disgust that Will would keep working construction and watching Pats games while Chuckie himself knows that's exactly what his own future holds is incredible.

The other side of this is the relationship between Sean (Robin Williams) and Gerald (Stellan Skarsgard). Gerald is a shitty friend who is obsessed with jealousy and image. The incredible screenplay by Damon and Affleck doesn't take a shortcut to make Gerald a traditional movie villain. He has the right intentions for Will. But, he also treats Sean badly and never attempts to understand why his old friend does what he does. It's a fantastic juxtaposition to seeing how much Chuckie cares for Will. For all of Gerald's brilliance, he'll never understand that.

It's this theme of friendship that make Good Will Hunting timeless. It feels almost as fresh now as it did when I sat in a Portsmouth, New Hampshire movie theater seeing it for the first time. The theater has long been torn down but the movie still is in our zeitgeist. It doesn't hurt that both Damon and Affleck have had great careers. But even saying that, they haven't reached quite this peak again in their careers. Affleck won Best Picture for Argo (but wasn't even nominated for Best Director) and Damon has been nominated for two other acting Oscars...but it's almost impossible to reach the heights of winning that screenplay Oscar together for this. It wasn't just winning the Oscar. It was what felt like an unlimited future for these guys.

TIMOTHY A. CLARY. Getty Images.

Minnie Driver is perfect as Skylar. She's a great counterbalance to Will Hunting, who truly doesn't think he deserves her. He chases after her in the end and I bet they do date when he gets out there. But, I don't see that being an eternal love story. That's not what this movie is. It's about Will breaking free of invisible chains he put on himself because he couldn't get past the pain of how he grew up.

I'm not the biggest Robin Williams fan of his comedy. His stand-up was too frantic and zany for me. But, he was one Hell of an actor. This is his greatest performance but watch him in Good Morning, Vietnam or Awakenings or Insomnia or Dead Poets Society. Even in Mrs. Doubtfire, you care about that family so much simply because he cares. Not many actors get nominated for four acting Oscars. One of the greatest actors of the 1990's is first thought of as a comedian by many. That's pretty impressive.

You feel like you know these characters. They feel like people you could meet in real life. None of them are perfect but none are truly bad either. They are people in very different circumstances doing the best that they can. It takes one Hell of a screenplay to make you care this much. Affleck and Damon may never reach quite these heights again, but who could?

4. Good Will Hunting

5. Casino

6. Groundhog Day

7. The Silence Of The Lambs

8. Office Space

9. The Sixth Sense

10. Boogie Nights

11. Jurassic Park

12. Jackie Brown

13. A Few Good Men

14. The Fugitive

15. The Truman Show

16. Fargo

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