1. Sidney Deane and Billy Hoyle from White Men Can’t Jump.
Why it’s easy: You could walk into any thrift store or Urban Outfitters and find everything you need for these costumes.
Why it’s awesome: White Men Can’t Jump is obviously one of the most iconic movies of our time and what makes it great is the love/hate relationship between street-ball hustlers Billy and Sidney — and their outfits.
Possible Downside: You have to backup all your shit talking.
2. Conor O’Neill from Hard Ball.
Why it’s easy: All you need is a leather jacket and an aura of scumbag.
Why it’s awesome: Who doesn’t want to be a degenerate gambler for one night? Also you get to date Diane Lane as a school teacher!
Possible downside: Finding a bunch of 11-year-olds who will be the Kekambas.
3. Shooter McGavin from Happy Gilmore.
Why it’s easy: All you need is a polo shirt and a superiority complex.
Why it’s awesome: You get to be the greatest villain in sports movie history.
Possible downside: You might get your ass kicked for simply being an asshole in a polo shirt.
4. Spike’s dad from Little Giants.
Why it’s easy: Wear dark military-esque t-shirt. Pour water all over your shirt. Be very demanding.
Why it’s awesome: Little Giants is the best and ladies love a meathead asshole who yells a lot, right?
Possible downside: People constantly doing pull ups on your arms.
5. Gordon Bombay from Mighty Ducks.
Why it’s easy: Put a name tag on a varsity jacket that says “Coach Bombay.”
Why it’s awesome: Quack… quack… quack… quack…
Possible downside: Your drivers license was taken away because your pesky DUI. Still hung up on a missed goal from Pee Wees.
6. Billy Beane from Moneyball.
Why it’s easy: All you need is a windbreaker.
Why it’s awesome: General managers are totally in right now.
Possible downside: You don’t look like Brad Pitt.
7. John Biebe from Mystery, Alaska.
Why it’s easy: Grow some scruff. Let your hair grow. Wear your entire winter wardrobe. Boom, you’re a legendary Alaskan pond hockey player.
Why it’s awesome: Um, legendary Alaskan pond hockey player. Need I say more.
Possible downside: If you live in a warm weather climate you might get sweaty.
8. Morris Buttermaker from Bad News Bears.
Why it’s easy: Put on a hat. Be crass. Drink beer.
Why it’s awesome: Being crass and drinking beer.
Possible downside: Getting too into character.
9. Lincoln Hawk from Over the Top.
Why it’s easy: Rip off the sleeves of your shirt and turn your hat around.
Why it’s awesome: You’d be a professional arm wrestler!
Possible downside: People actually challenging you to arm wrestling competitions.
10. Chet Steadman from Rookie of the Year.
Why it’s easy: Mustache.
Why it’s awesome: He’s the giver of cheddar — the high stinky limburger.
Possible downside: Channeling Gary Busey is like opening pandora’s box. You just don’t know what might happen.
11. Lucas McNamara and Caleb Mandrake from The Skulls.
Why it’s easy: Act like an Ivy League boxer and rower. Wear your normal clothes.
Why it’s awesome: Secret societies are really fucking cool.
Possible downside: Duels.
12. Ryan Dunne from Summer Catch.
Why it’s easy: All you need is a baseball hat, lawn care shirt and bad attitude.
Why it’s awesome: Jessica Biel is your girlfriend, you live in Cape Cod and you get signed by the Phillies.
Possible downside: Need to be lefty. Debilitating inferiority complex.
13. Anyone from Hoosiers.
Why it’s easy: All you need is a tank top and shorts.
Why it’s awesome: Underdog stories are the best.
Possible downside: Short shorts.
14. Bill Murray from Space Jam.
Why it’s easy: All you need is a Hawaiian shirt and a head umbrella.
Why it’s awesome: You get to be Bill Murray.
Possible downside: You’re not as funny as Bill Murray.
15. Mike O’Hara and Jimmy Flaherty from Celtic Pride.
Why it’s easy: Wear a Jazz jersey and root for the Celtics.
Why it’s awesome: Um, I’m not totally sure.
Possible downside: Kidnapping is a crime.
16. Irving Blitzer from Cool Runnings.
Why it’s easy: All you need is a Jamaica scarf and a slight weight problem.
Why it’s awesome: Your the coach of the first Jamaican bobsled team.
Possible downside: Not being able to afford a sled.
17. Roy Munson from Kingpin.
Why it’s easy: Like all Woody Harrelson movies, you can get the whole outfit at a thrift store.
Why it’s awesome: Bowling.
Possible downside: Finding a fake right hand.
18. Paulie from Rocky.
Why it’s easy: Dress like a homeless man. Smoke a cigar and carry a bat.
Why it’s awesome: It’s very easy to be a drunk angry guy with a bat.
Possible downside: No one likes Paulie.
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