5. Major League
Stars: Tom Berenger, Charlie Sheen, Wesley Snipes, Bob Uecker
Baseball is America's most revered pasttime, even if the popularity of the sport is waning, and it's brought to the big screen in truly funny fashion in this perfectly cast movie about the down in their luck Cleveland Indians. Filled with memorable characters and gags galore, this baseball movie transcends time as one of the best in it's field.
Stars: Woody Harrelson, Randy Quaid, Vanessa Angel, Bill Murray
Who doesn't love bowling? It's uniquely America's sport because everybody can just drive over to the local lane, grab a ball, and wing it at some pins to the delight of everybody…and it doesn't matter if you hit a one! In Kingpin, this sport is taken to the hilarious edge as Woody Harrelson is at his disgusting best as one handed bowler Roy Munson looking to get some payback and some cash in coaching up amish bowling phenom Ishmael Boorg, played masterfully by Randy Quaid.
Stars: Vince Vaughn, Christine Taylor, Ben Stiller, Rip Torn, Justin Long
I'm not a huge Ben Stiller fan but Vince Vaughn and company carry his shaky performance in this masterful homage to the sport that terrorized my childhood and the childhood of many an American who can't throw a ball, dodgeball. Dodgeball is a true underdog movie and one that isn't going to go down as anything but funny. It does have one of the most memorable lines of all time, uttered by Rip Torn as he is training Vaughn and his team. “If you can dodge a wrench, you can dodge a ball.”
2. Happy Gilmore
Stars: Adam Sandler, Carl Weathers, Julie Bowen, Allen Covert, Christopher McDonald
This is the greatest movie that Adam Sandler put out, in my opinion. It's a gut wrenching look at a hockey player wannabee who finds out he can drive a golfball far enough to make even Tiger Woods look amateurish. Throw in some anger issues, a quirky nemesis, Bob Barker getting beat up and a pesky alligator and you have a recipe for immortality.
Stars: Chevy Chase, Rodney Dangerfield, Ted Knight, Michael O’Keefe, Bill Murray
Caddyshack is the king of the sports comedies, period, and it will never be dethroned. This comedy centers around the golf course but is filled with such a diversity of stories and gags that it actually seems like it's more an event than a film. With a cast of comedy legends, nothing but greatness could have been expected and even with those lofty goals, this movie transcends them into genius and is forever timeless. If you haven’t watched it, do so.