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.

stool-and-starsFeatured on Barstool
Video Player is loading.
Current Time 0:00
Duration 0:00
Loaded: 0%
Stream Type LIVE
Remaining Time 0:00
 
1x
  • Chapters
  • descriptions off, selected
  • captions and subtitles off, selected

    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.

    Giphy Images.

    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?

    Giphy Images.

    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