Top 100 Movies Of The 1990's: #51 Happy Gilmore
Box Office: $38.8 Million
Oscar Nominations: None
Oscar Wins: None
MovieRankings.Net: 82/100
Available To Stream: Peacock, Amazon Prime ($4)
For years, I had Billy Madison ranked ahead of Happy Gilmore. But in the last few years, I have found Happy Gilmore to be the better and more complete movie. Are both pretty stupid movies? I guess but they are also both at making me laugh my ass off for almost 30 years now. I saw both of these in the theaters when they came out and I still think they are both still fantastic comedies. I know some people reading this will be disgusted that I have Happy Gilmore ahead of Braveheart. It's a fair complaint but I'm trying to give comedies the respect they deserve here. In my opinion, Happy Gilmore is better at what it is trying to do than Braveheart is.
Brandon and I had a similar debate about a drama vs. Happy Gilmore on Double Play (RIP):
It's hard to believe now but Happy Gilmore really wasn't a hit in the box office. It never hit #1 in the box office. It opened at #2 (behind Broken Arrow, the John Travolta/Christian Slater action movie in its 2nd week in release). Happy Gilmore didn't even make $40 million dollars. That's still enough to make a profit but this wasn't a massive blockbuster like Big Daddy and The Waterboy were. It wasn't until The Wedding Singer (#99) did Sandler have his first $80 million dollar movie.
This was the first partnership between director Dennis Dugan and Adam Sandler. Dugan has never been a critical darling. He's been nominated for four Razzies. Yet, people go and see his movies. Dugan has directed six movies* that have gotten $100 million dollars or more. Martin Scorsese has only directed four $100 million dollar movies.
(*Big Daddy, I Now Pronounce You Chuck And Larry, You Don't Mess With The Zohan, Grown Ups, Just Go With It and Grown Ups 2)
Shooter McGavin is the best villain in Adam Sandler movie history. Christopher McDonald is so perfect as the slimy rich golfer. It's such perfect casting. Happy Gilmore might even have the second best villain with Ben Stiller as the orderly in the nursing home. Literally every line he says has me laughing out loud. Having these two in the movie is such a great added element that separates this from other comedies.
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This is my favorite Adam Sandler comedy of all-time. I do have Uncut Gems slightly ahead of it but I also don't count that as a comedy. The casting choices in Happy Gilmore are so perfect. Carl Weathers mocking his Apollo/mentor character in Rocky III/Rocky IV. Frances Bey is such a perfect grandmother. Julie Bowen seems to be having fun as the love interest. Bob Barker is all in on the joke. It's such a perfect job of casting.
The fish out of water concept with Sandler as a hockey player turned golfer could feel tired with someone else at the wheel. Instead it felt so fresh and fun the first time I saw it. Now, it's more of a perfect movie to throw on at nearly anytime. It's consistently entertaining. It's a movie I think I'll be watching every year or so for the rest of my life.
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