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. 

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