Adam Sandler Characters Ranked: Where Does Happy Gilmore Land 30 Years Later?

Back in February 1996, Adam Sandler first graced the big screen as a short-tempered hockey player-turned-golfer named Happy Gilmore. Coming in the wake of Billy Madison, the sophomoric sports comedy cemented Sandler as a Hollywood megastar. So where does Happy Gilmore rank among the most iconic characters of Sandler’s career as the film hits its 30th anniversary?

Check out DraftKings’ rankings of Sandler’s top 5 movies here!

10. Lenny Feder, Grown-Ups

While the Grown-Ups films are far from high art, they do stand in for a massive piece of Sandler’s identity in the 2010s. Larry isn’t the most well-defined or quotable character, but he does fit perfectly into Sandler’s so-called dad era. Sandler has been taking on plenty of family man parts over the past decade-plus, and this is arguably the urtext in that category. Ironically, his performance in Happy Gilmore 2 is just as much Lenny Feder as it is Happy Gilmore. He’s goofy, but more corny than abrasive at this point in his career. The annoying supporting performances and horrible sequel ultimately drag down the legacy of what is an otherwise solid studio comedy from Sandler, one that has permeated throughout the rest of his filmography.

9. Longfellow Deeds, Mr. Deeds

Mr. Deeds owes so much to Sandler’s early work, since he settles right back into the man-child personality that made him popular in the mid-90s. And yet, Longfellow Deeds is sweet and kind-hearted where his previous roles were angrier and crueler. Mr. Deeds is far from Sandler’s best or most iconic rom-com, but his title character is an interesting evolution of the Billy Madisons and Happy Gilmores of the world. But don’t get me wrong, he’s still as loud and grosser as ever, just with some of the edges sanded off.

8. Stanley Sugerman, Hustle

As the first non-comedic role on this list, Sandler’s performance as Stanley Sugerman proved he still has the chops in 2022. The countless cameos in Hustle aren’t special amid Sandler’s filmography, but the way Sandler bounces off of them just might be. The connection Stanley forms with Bo Cruz – played by former Nuggets and Timberwolves big man Juancho Hernangómez – is earnest and somehow still plausible. Sandler really sells Stanley’s desperation as a 76ers scout hanging on by a thread, anchoring a movie that is an otherwise standard entry into the sports movie genre.

7. George Simmons, Funny People

Funny People is not Sandler’s best film, nor is it director Judd Apatow’s. It’s a little too long, saccharine and unfocused on the whole. At the same time, it is a quintessential mid-2000s dramedy. It plays with Sandler’s celebrity status and public persona, commenting on his career in a bold and melancholic fashion. There are few actors who could pull off this role, while Sandler gets to effectively play himself. As an A-list comedian with a terminal illness, reflecting on his life, lost loves and how to pass the baton to the next generation, Simmons is layered in a way that sheds a light on how both Sandler and Apatow view the industry and the titans of comedy inside of it.

6. Robbie Hart, The Wedding Singer

Pain personified.

None of Sandler’s characters take on heartbreak quite like Robbie Hart. And where some express themselves through anger and sometimes physical altercations, Hart uses the power of song (which is sometimes rage-filled and occasionally followed by a brawl.)

Above all else, Hart gave Sandler the opportunity to further lean into his comedic musical abilities.

5. Barry Egan, Punch-Drunk Love

Coming off the critically-acclaimed trio of Hard Eight, Boogie Nights and Magnolia, director Paul Thomas Anderson apparently wanted to work with one actor above anyone else. Sandler was PTA’s muse for Punch-Drunk Love, and the result was a lovable, lonely romantic in Barry Egan. Sandler is not a traditional romantic lead, though, and Egan is not written to be one. He is overlooked and berated by his family, painfully shy and disturbingly angry underneath. Sandler takes all of that and runs with it, managing to yearn for Emily Watson’s Lena Leonard in a way that is both fantastical and down-to-earth. While the film’s most memorable scenes involve Sandler blowing his lid opposite Philip Seymour Hoffman, the romance that Sandler brings as Egan is what makes it an all-time classic.

4. Bobby Boucher Jr., The Waterboy

Sandler’s characters are known for the humor they bring to the big screen, but there are also a few who you absolutely don’t want to cross.

Happy Gilmore is a loose cannon and Little Nicky is obviously overpowered, but Bobby Boucher is the sleeping giant that you can’t afford to awaken. (And that’s without factoring in his wrathful girlfriend, Vicki Vallencourt.) One half of the toughest on-screen couple you’ll come across, Boucher is so memorable that decades after his movie, you can still buy his South-Central Louisiana State University jersey online.

He was also lightyears ahead of the sports world. The power of visualization seemed as ridiculous as the medulla oblongata until 1998. And now, thanks to Boucher, we know both are completely legit.

3. Howard Ratner, Uncut Gems

Uncut Gems is simultaneously a departure for Sandler and a perfect avenue for the star to channel his best traits as a performer. Sandler could not be a more perfect fit in the chaotic, anxiety-ridden world built by the Safdie Brothers, even if it took an unusually unflattering performance for him to get there. Howard is arrogant and confident to a fault, never backing down even when it’s clear he is in over his head. A small-scale jewelry dealer shouldn’t be starting feuds with Kevin Garnett or The Weeknd, but Howard just doesn’t know when to quit. Sandler didn’t earn an Oscar nomination for playing the self-destructive gambling addict, but he arguably should have won the award.

2. Happy Gilmore, Happy Gilmore

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1. Billy Madison, Billy Madison

If we’re being completely honest, Happy Gilmore is very iterative of Billy Madison. Sandler’s title role in his 1995 breakout hit is effectively the basis for his entire early-career identity, inspiring his many immature, charming performances in the years that would follow. Happy Gilmore may have aged better as a film and become more of a staple in pop culture, but it’s hard to overlook the influence and importance of Billy Madison. He is an anti-establishment jerk, albeit one who has a heart of gold. If that doesn’t scream Sandler, I don’t know what does.

Honorable Mentions: Sonny Koufax in Big Daddy, Dracula in Hotel Transylvania, Dr. Henry Roth in 50 First Dates