The Happy Gilmore 20th Anniversary Character Power Rankings

Is it the greatest sports-comedy ever made? No, probably not. Is it even the greatest golf-comedy ever made? Again, no. (“Caddyshack” probably still holds both belts). But “Happy Gilmore” is certainly a sports-comedy of the highest quality, and easily the best of Adam Sandler’s films.

This week marks the 20th anniversary of a comedy staple of the 90’s that’s defined both Sandler’s career and the sports comedy genre ever since.

It engendered an entire generation of casual golfers to play like jackasses. Seriously, any guy between the ages of 17 and 35 has certainly pissed off legit golfers across the globe by emulating the ridiculous wind-up running drive, the profanity-laden meltdowns, and the surprisingly helpful hockey-style putt.

What really makes this movie memorable, however, is the slew of cartoon characters and bit players who flow through the movie spewing brilliant one-liners and basking in the glory of the shenanigans. Who garners the biggest laughs? Who wins every scene? Who makes the movie go? Who makes “Happy Gilmore” Happy-freaking-Gilmore?

It’s a question that simply must be answered.

So without further adieu, let’s celebrate the 20th anniversary of “Happy Gilmore” with the completely inessential and wholly arbitrary “Happy Gilmore” 20th Anniversary Character Power Rankings.

Editors Note: Though he’s not my favorite character in the movie, I felt uncomfortable slotting Happy anywhere but first. The whole movie revolves around him, and with the perfect mix of swarm and charm, it’s easily Adam Sandler’s best comedic performance. So, instead of trying to build a list that inevitably built up to the main character, I removed him from the process all together. Consider him #1A if you must, but for the purposes of this thought exercise, he simply can not be included. (I’m taking this way too seriously).

10. TIE: Happy’s First Caddy, Happy’s second Caddy

Played by: Jared Van Snellenberg (who?) and Allen Covert (again, who?)


Ok, so I’m cheating already. I needed both on this list but couldn’t figure out how. So I combined them and let them tie for the last spot.

The former is mostly around just so Sandler can slap around a dorky kid, including the great choke-hold shake-down celebration when Happy wins his first major open. Meanwhile, the latter, a schlubby homeless man who stays mostly mute the entire flick, provides excellent visual comedy as he helps Happy win the Pro Golf Tour. In one scene, he uses a cracker as a marker on the green, only to eat it. In another, he cleans some underwear in the ball washer while golf-snobs look on.

These two guys don’t add much, but give Sandler plenty to play off of.

9. The Mister-Mister Lady

Played by: Helen Honeywell

BEST QUOTE: “Mister! Mister! Get me out of here!”

Perhaps the best pound-for-pound player in the entire movie. She pops up for two quick scenes, and instantly steals both. As the unfortunate victim of old-people home abuse, she begs Happy to help her escape. Later, she is nearly crushed to death (actually, it’s insinuated that Happy “may have killed her”) via a falling air-conditioning unit.

She only shrieks. But just thinking about her now is making me chuckle.

8. Grandma

Played by: Frances Bay

BEST QUOTE: “Who are you waving at, Happy?”

She’s the emotional center of the movie. In many ways, she represents why “Happy Gilmore” succeeds when so many other Sandler movies failed. She brings heart to a usually heart-less and mean-spirited guy. Plus, she rocks a Gene Simmons KISS mask when we first meet her, and totally hams it up when Happy describes her advanced age…

“She’s… too old!”

7. Mr. Larson

Played By: Richard Kiel

BEST QUOTE: “Hey Shooter, you forget your 9-Iron?”

Standing at 7’2”, Kiel grew to fame playing monstrous Bond villains in the 70’s. But it’s his turn as Happy’s delightfully encouraging, nail-in-head toting, golf-club bending, hulking Frankenstein of a former boss that I’ll always remember him as.

His best moments come from harassing the snobby Shooter McGavin, specifically when his foot is struck by and errant Shooter drive, making the “play the ball as it lays” rule all the more complicated.

6. The Alligator

Played by: N/A


This one-eyed chomper gets a full-circle joke that’s entirely satisfying, and adds a surprising amount of depth to the “Happy Gilmore” mythos. (As someone who spent 3 years as a pretentious high school newspaper film critic, I never ever ever thought I would’ve written the previous sentence).

First off, we learn he cut Chubbs’ career short by biting off his damn hand.

Later, we run into him again, when Happy recognizes him from the missing eye, and what ensues is one of the great man vs beast WWE-inspired matches ever captured on film. After stealing Happy’s ball, this devious reptile receives a number of people’s elbows before finally succumbing to Happy’s knockout, head-butt blow.

And after all that, we learn Chubbs startles easily when his bitter enemy’s severed head, meant as a purifying gift, sends the one-handed former golfer out a two-story window to his untimely death.

Oh, the irony of it all. Happy decapitates the alligator to avenge his mentor. His noble act of cross-species homicide is what directly caused Chubbs’ death. Violence is a circle. Who would’ve thought Sandler could be so damn Shakespearean?

5. Chubbs

Played by: Carl Weathers

BEST QUOTE: “Quit acting like a damn fool!”

Mr. Myagi. Patches O’Houllahan. Clint Eastwood from “Million Dollar Baby.” Great sports movies always feature great mentors. It’s one of the defining aspects of the timeless formula.

“Happy Gilmore” is no exception, and Chubbs is a great sports movie mentor. From his constantly destroyed fake wooden hand, to his epic alligator feud, Chubbs offers invaluable coaching and insight to our titular hero throughout his journey.

He’s got the eye of the… er… alligator (literally). And, I must admit, I’ve heeded his advice and desperately searched for my “Happy Place” in moments of pure sports frustration. I know I’m not alone on this one.

4. The Heckler

Played by: Joe Flaherty

BEST QUOTE: “You will not make this putt, you jackass!”

This video is every reason this guy is funny. Anyone who’s ever golfed ever has stolen at least one of the heckles from his endless barrage of insults.

He’s so unnerving, unsettling, and ultimately hilarious.

He may be obnoxious, but admit it, you chuckle at every one of his quips… you jackass!

3. Bob Barker

Played by: Bob Barker

BEST QUOTE: “I don’t want a piece of you, I want the whole thing!”

As Happy’s partner in the celebrity doubles tournament, “The Price is Right” host gets an extended cameo that concludes with a completely memorable brawl. In a movie peppered with hockey-goon inspired punch-out’s, old-timer Barker duking it out with Happy easily tops the list.

His endless frustration is palpable as Happy’s game deteriorates in front of his eyes, proving Barker has real comedic chops that can extend farther than just game show host. Plus, he tees up the great one-liners in movie history… “The Price is Wrong… bitch.”

2. Hal L. (A.K.A., the retirement home employee)

Played by: Ben Stiller

BEST QUOTE: “Well now your back’s gonna hurt, cause you just pulled landscaping duty.”

Ben Stiller, in sneakily one of his funniest roles, is the small, nasally employee at the nice retirement facility who ends up being the most despicable character in the entire movie. The man runs a tight ship, with no time to spare to serve glasses of warm milk to his elder patients, as he manages what may or may not be a black market quilting business. Don’t try to escape. Don’t try to tell loved ones of the atrocities of the nursing home. Don’t even try to lack off on the job. Because any dissenting voices will get reassigned to punitive landscaping duty.

1. Shooter McGavin

Played by: Christopher McDonald

BEST QUOTES: Too many to name.

Shooter might just be the most tragicomic character in the entire film. He’s an excellent golfer who spent years paying his dues. He’s finally ready to win the ever elusive “Gold Jacket” when out of nowhere comes no-name Happy Gilmore.

Sure, he was kind of a dick, but he didn’t have time to iron out his personality flaws. As he puts it, “he was too busy winning.” He’s driven to sheer villainy and near insanity, but who wouldn’t be. It was his turn to win, when all of the sudden some clown rolls around, sucks away all the media attention, and beats him at the one thing he spent his entire life training for. It’s quite sad, in a way.

But Shooter’s snark and desperate attempts to out-cool and out-charm Happy lead to some of the best scenes in the movie. McDonald owns the role, owns every scene he’s in, own’s the movie, owns one of the great all-time sports movie character names, and now own’s the coveted number one spot on The Happy Gilmore 20th Anniversary Character Power Rankings.


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