Ranking The Love Interests In Adam Sandler Movies Based On How Absurdly Out Of His League They Are

adam sandler movies love interests unrealistic


Adam Sandler is a national treasure, and as far as comedians are concerned, he’s up there with the likes of Paul Rudd, Larry David, and John Mulaney as some of the objectively likable guys in the game who could all compete for the title of “America’s Dad” (he probably has a leg up on those last two when you consider David is firmly in “Grandad” territory and Mulaney gives off a bit of a “pubescent teen trapped inside the body of a 38-year-old” vibe).

However, The Sandman has yet to be awarded the title, which may possibly have something to do with the fact that the last guy the United States slapped that label on wasn’t exactly the wholesome patriarchal figure he was painted as. Interestingly enough, the actor got his first big break after landing a recurring role on The Cosby Show, and (as my finance friends would say) his career has only gone up and to the right since then.

Unlike Cosby, Sandler doesn’t dole out life lessons on a weekly basis, as he uses his movies as a conduit as opposed to a network sitcom. However, I think most people who watch his more recent works or are just familiar with who he is as a person can see a little bit of their own father in him, whether it’s the dad jokes, the dad bod, or the virtually nonexistent amount of effort he puts into assembling his outfits before appearing in public.

Embed from Getty Images

As a result, he can establish a connection with a modern audience because he’s just an average-looking middle-aged man who just so happens to have one of the most illustrious careers of all time.

Since getting his start in the late 1980s, there’s really nothing Sandler hasn’t done. He leveraged his success as a cast member on Saturday Night Live to take his talents to Hollywood while also pumping out albums and specials that managed to birth some of the best musical comedy you’ll ever encounter. Of course, his acting is what put him on the map and what’s allowed him to stay there for decades, as he has over 80 television and movie acting credits on IMDb in addition to the many other projects he’s put his fingerprints all over thanks to his writing and producing contributions.

However, when everything is said and done, he’ll largely be remembered for “Adam Sandler Movies,” a subgenre that the world first became familiar with when he followed up the release of Billy Madison in 1995 with Happy Gilmore a year later, kicking off a run of movies revolving around the man-children he’d frequently portray.

Those aforementioned projects would each lend part of their name to the production company he founded in 1999, and there’s a certain aura to a Happy Madison film that makes it obvious you’re watching an Adam Sandler Joint. In a way, he’s followed Quentin Tarantino’s “If it ain’t broke, don’t fix it approach” over the past 25 years, just with more juvenile humor and much less of an emphasis on close-up shots of people’s feet.

Of course, Sandler’s comedic films haven’t exactly been showered with awards and accolades, but as is the case with Tarantino, you basically know what you’re going to get by now. His most recent release, Hubie Halloween, was no exception.

If we’re being honest it wasn’t great (I’d personally say it’s one of his worst movies to date), but at the end of the day, it was basically everything you’d expect from an Adam Sandler movie these days: moderately entertaining with a few particularly amusing moments and featuring the tried-and-true “let’s get as many famous people as we can in the cast and throw them all in the trailer to get people to watch it” approach to lure viewers in.

It worked (at least on me), and while I was led to believe Kevin James, Steve Buscemi, and Ben Stiller would have some major screen time, it felt like almost every scene featuring a “big-name actor” could’ve been condensed into a TikTok video. It also featured a number of throwbacks to his previous stuff, as if the reasoning was, “Well, people liked these characters and jokes before so let’s just bring them back and hope for the best,” which only worked out if your definition of “best” is dramatically different than how it’s traditionally used as a metric for success.

Did I still watch it the same day it hit Netflix? Of course I did, and it was during that viewing session that I came up with the idea for this piece. Hubie might’ve been a mentally-handicapped 45-year-old who still lives with his mom and has an almost unhealthy obsession with Halloween, but that didn’t stop Julie Bowen’s character from falling madly in love with him.

Now, it’s no secret Sandler’s movies have always featured incredibly attractive love interests, so while I tried to suspend my disbelief here, this just felt particularly absurd. It might have something to do with the fact that I’ve been single for three years and the current state of the world has made it a bit difficult to rectify that issue, but I couldn’t really get over just how ridiculous it was.

Sandler might be 54-years-old but it’s not like he was really a top contender for People‘s “World’s Sexiest Man” honors at any point in his career, which makes you wonder how his characters have been able to pull some of the hottest women in Hollywood for over two decades. I know most of his movies have a pretty ridiculous premise but the fact that a hugely-famous and drop-dead gorgeous actress ends up falling for him in almost every single one is just patently absurd.

As a result, I found myself reflecting on all of the other occasions where Sandler’s character is either married to, dating, or in the process of winning over an absolute bombshell, which resulted in me digging through his filmography to reflect on just how out of his league all of his fictional love interests have been before deciding to whip up together a list ranking just how improbable these couplings would be in real life.

It’s worth noting I didn’t focus solely on Sandler’s looks (or lack thereof) but on his character as a whole. However, at the end of the day, humans are incredibly vain, and if you’re not physically attracted to someone, their other qualities are kind of a moot point. This list also revolves around the “Adam Sandler Movies” that exude his signature style as opposed to “Movies that Adam Sandler Is In”; you know, the ones where he shows off his chops as A Serious Actor featuring a notable lack of jokes revolving around bodily functions.

So, without further ado, I present “The 10 Most Unrealistic Adam Sandler Movie Relationships”

10. I Now Pronounce You Chuck & Larry (Kevin James)

adam sandler movies love interests unrealistic


What? You thought it was only going to be women? Come on, guys. Sandler is a progressive free spirit who doesn’t conform to society’s rules—especially if it’s for tax purposes.

In I Now Pronounce You Chuck & Larry, Sandler “marries” Kevin James, his best friend in the movie (and probably in real life) to save money courtesy of a legal loophole. As far as his films go, this one is comparatively profound when it comes to the issues being tackled, as it sheds light on rampant homophobia, the role of the government in our personal lives, and the flaws in America’s tax system.

I’d be a bit surprised if everyone who made it was actually trying to be deep. They probably just thought it was funny to have two firemen marry each other when they weren’t actually gay…and it was—especially when Sandler’s character (a known ladies man) has to act like he’s not interested in Jessica Biel, who plays the lawyer who helps them navigate the system.

adam sandler movies love interests unrealistic


Even if we were framing Biel as the love interest here, I think it’d still rank fairly low because Chuck was known for being a frequent and great sex-haver. She may have been a successful attorney, but he was also a fireman, and I’m told women love a man in uniform. However, the real reason this comes in last is that I don’t only think Sandler could’ve pulled James here but was arguably out of his league (but that’s a list for another time).

9. Grown Ups (Salma Hayek)

adam sandler movies love interests unrealistic


This is a very believable match for a few reasons.

First off, Sandler is basically playing himself. There are no weird voices or over-the-top tantrums; it’s just “Funny Guy Adam,” who is still a pretty normal-looking dude but far from the schlub he’s played in other movies. Sure, Hayek might still have the upper hand in the attractiveness department but we can’t ignore the other factors in play.

Sandler’s character is an extremely wealthy Hollywood agent, as evidenced by the fact that he had enough money to pay for the vacation he goes on with his old buddies with their families in tow. With pockets that deep, you can open up plenty of doors that make it a bit easier to find a wife and it’s not too far-fetched to believe he’d be able to woo a fashion designer with an irresistible accent.

If I had to guess, Sandler’s character spent a few years blowing his money on high-end escorts and bottle service that led to plenty of one-night stands before finally finding Hayek, a woman he felt he could settle down with and who gave him an excuse to leave behind a life that largely revolved around strip clubs and cocaine. That, my friends, is what true love looks like.

8. Happy Gilmore (Julie Bowen)

adam sandler movies love interests unrealistic


At first glance, this seems pretty unrealistic. A degenerate hockey player-turned-professional golfer who couldn’t care less about the game’s etiquette matched with a purist of the sport who was probably raised on the course by incredibly WASPy parents? It doesn’t make sense.

However, Happy is the key to helping Virginia realize there’s more to life than golf, and when she finally discovers there are prospective suitors to be found outside the confines of stuffy clubhouses, she decides to rebel a bit—and what better way to do that than date the guy who is turning the game on its head and making life hell for Shooter McGavin, whom she hates as much as Gilmore does?

She gets to mentor Happy in his newfound profession while not only remaining close to the game she loves but sticking it to a father I invented for the purpose of a backstory that may or may not be true. Additionally, Happy managed to make quite a name for himself on the tour, so when you combine the oversized novelty checks he began collecting and the free sandwiches she’d have access to after he landed a Subway sponsorship, she stands to benefit a great deal.

Side Note: I was shocked when doing research to find out Virginia’s last name was “Venit” and not “Bennet.” It didn’t leave me “The Bears’ last name is actually ‘Berenstain'” levels of shook but it was still a lot to process.

7. Billy Madison (Bridgette Wilson)

adam sandler movies love interests unrealistic


Of all of the Certifiably Dumb People that Sandler has played over the years, Billy Madison‘s eponymous protagonist is arguably the biggest buffoon of them all.

In the movie, the actor portrays the son of an extremely successful hotel owner who (as children of filthy rich people tend to do) coasted his way through life expecting to take over the family business when his dad retired.  However, he finds himself in a pickle after being informed he has to graduate from high school to prevent one of his father’s partners from taking control and is given three months to make his way from first grade to his senior year and secure a diploma.

The love interest in Billy Madison is third-grade teacher Veronica Vaughn, who he becomes smitten with shortly after arriving at elementary school. It’s very important to remember he was a 27-year-old guy who was still pranking his neighbors by lighting bags of shit on fire outside their door and who needed 30 seconds to figure out how to spell the word “couch,” so to think he would possess the skills to talk to women when his only real previous exposure to them was through the nudie magazines he was so fond of is a bit of a stretch.

Veronica is undoubtedly a knockout (especially if you’re into certain types of role-playing) and Billy is undoubtedly one of the dumbest people—student or otherwise—she’d ever encountered. However, it’s important to remember A) The news has taught us plenty of teachers end up developing a thing for some of their pupils and B) There was likely a nice chunk of change waiting for him once he satisfied the terms of his agreement with his dad.

Improbable? Yes. Impossible? Well, based on how everything played out in the movie’s universe, apparently not.

6. Murder Mystery (Jennifer Aniston)

adam sandler movies love interests unrealistic


If you haven’t seen Murder Mystery, it’s actually pretty solid. In the movie, Sandler and Aniston are a married couple who find themselves on a boat only to experience one of those classic “Someone Got Murdered While The Lights Were Out” situations that we’ve all experienced at least once.

Sandler’s character, Nick, isn’t rich but he is a cop, so I’m assuming this could be a Chuck & Larry scenario where Aniston’s Audrey has a thing for the guys in blue. The movie also takes place shortly after the two celebrated their 15th wedding anniversary, so for all we know, Nick could’ve been a stud back in the day before transforming into the adequately attractive man he became. We also can’t rule out that a gun wasn’t the only heat he was packing down there, so this one might not really be as crazy as it seems

5. The Waterboy (Fairuza Balk)

adam sandler movies love interests unrealistic


Bobby Boucher gives Billy Madison a real run for his money here when it comes to what he has (or doesn’t have) going on upstairs. He’s certainly not the sharpest tooth in the alligator’s mouth, and while he might have some signature Southern charm, I think he takes the L as far as looks go between the two. However, while Fairuza Balk is by no means unattractive, she’s definitely one of the more believable love interests on the list, and when you factor in the fact that her character Vicki has been imprisoned multiple times, the intellectual gap is probably narrowed a bit.

Now, Bobby didn’t go to the University of Louisiana to play school; he went to play football. For him, girls were an afterthought. He probably could’ve cashed in on his jock status, but he opted to pursue his childhood crush even though Vicki seems like the kind of girl who would spend gameday listening to Fall Out Boy in her dorm room while reading Foucault.

However, what makes this slightly believable is that she knew him before he became a football star and saw him as more than that. Sometimes opposites attract, and when you consider they ended up married and riding a lawnmower into the sunset, I think it’s safe to say that’s what happened here.

4. Big Daddy (Joey Lauren Adams)

adam sandler movies love interests unrealistic


Big Daddy revolves around Sonny Koufax, a law school grad-turned-degenerate gambler who refuses to take the bar exam and suddenly finds himself with custody of his friend’s bastard child only to find love as a result.

As someone who’s a bit too intimately familiar with sports betting, there’s no way I could ever see this playing out in real life. Adams’ Layla Maloney is a legally-licensed lawyer with plenty of options to choose from who opts to go for the one with no possible happy ending. Sure, it might start out fine, but it’s only a matter of time until he’s slipping cash out of her purse to place a bet he’ll inevitably lose thanks to “the god damn Jets.”

Maybe I’m wrong; maybe he did truly become a changed man by the end and will continue to be the good dad that Layla fell for. She still probably could’ve done a lot better (which could not be said for Sonny), so while I like to think everything worked out for the best, there’s still a ton of potential for a Big Stepdaddy sequel based on how things probably played out.

3. Just Go With It (Brooklyn Decker & Jennifer Aniston)

adam sandler movies love interests unrealistic


Sandler threw a couple of punches above his weight class in Just Go For It, where he plays Danny, a 45-year-old plastic surgeon who is chasing Decker’s Palmer for 98% of the movie (interestingly enough, she’s a sixth-grade teacher, which, between this and Billy Madison, provides us with a bit of insight into the actor’s fantasies without broadcasting it to the world like Tarantino does with his foot fetish).

No matter how you cut it, this doesn’t make sense. Maybe Palmer wanted some work done that a teacher’s salary couldn’t pay for, but even if there was some kind of arrangement in place, I just don’t see someone with the looks to earn a spot on the cover of a Sports Illustrated Swimsuit Issue settling for Sandler’s character regardless of how successful his practice is.

In the end, however, he realizes he’s been in love with his receptionist Katherine (Aniston) the entire time. It’s slightly more believable but still seems fairly unlikely. I can only assume that this employee-employer relationship morphed into some sort of Stockholm Syndrome situation that led to them getting together before the credits rolled.

2. Hubie Halloween (Julie Bowen)

adam sandler movies love interests unrealistic


As I mentioned, Adam plays Hubie, a clueless, Halloween-loving incel who is not very smooth in any area of life. He did say he had a girlfriend in Canada but she weirdly never made an appearance. Regardless of his immaturity, the very attractive 50-year-old Violet (played by Bowen) was deeply in love with him.

Violet peaked in high school, going from a prom queen who married her high school sweetheart to a waitress at the town diner. In the movie, no one knows why she likes him, because if we’re going off “The Scale,” she’s probably a 9 and he’s a soft 2 at best. Nevertheless, she thinks there’s something “sweet” about him and even had the audacity to say she’d always loved him.

The lead cheerleader falling in love with the nerd isn’t a totally impossible scenario, but if we’re assuming she did actually have a thing for him in high school and didn’t just look at him as a rebound after getting divorced 20 years later, I’m not buying it. Sure, she may have once thought, “Oh, ‘The Hot Girl and The Nerd’ Would be a fun one-time thing to do just to say I did it,” but they would never actually get into a relationship. That’s crazy talk.

The two still end up together because whatever town this place takes in is not bound by the rules of reality; a place where she went from dating a star quarterback to a glorified hall monitor when she probably could’ve ended up with a dude who works at J.P. Morgan if she’d tried a little harder.

1.You Don’t Mess With the Zohan (Emmanuelle Chriqui)

adam sandler movies love interests unrealistic


As someone who was a big Entourage guy during my formative years, I’m still convinced that Sloan may be the most attractive person of all time. It was already a stretch to believe she’d dated all 5’4″ of Eric in the show, and now we’re supposed to buy into the notion she’d go out with an employee at her small hair salon? Give me a break.

Sure, Zohan has some weird superpowers and is actually pretty damn ripped but he’s also one of the most ridiculous-looking characters Sandler has ever played (it’s also safe to say the profession he pivoted to isn’t exactly as lucrative as the counterterrorism career he abandoned). I mean, I guess he could just be her type but I just feel like the casting director didn’t even try to justify this pairing when they decided to have Chriqui play Dalia.

I also don’t want to wade too deep into the political waters here, but the fact that we eventually discover she’s the sister of the Palestinian terrorist Zohan was trying to take down is really the icing on a cake that’s impossible to digest. Sure, the “love conquers all” message might be nice and heartwarming but the fact that there was any love here in the first place is something I just can’t wrap my mind around.

Honorable Mention: Uncut Gems (Julia Fox)

adam sandler movies love interests unrealistic


I didn’t count this one because it’s not a typical “Adam Sandler Movie,” but after a conversation with my team, we decided to include it.

On paper, it doesn’t check out. Howard is a wannabe gangster who’s still rocking diamond studs at the age of 54. His mistress (Fox) was an employee at his shop who absolutely loved him to a point where she even passed up the opportunity to hook up with The Weeknd to be with him, which was a crazy move on her part (of course, if she had really loved him, she wouldn’t have tried to hook up with the Canadian Michael Jackson in the first place but that’s neither here nor there).

Like I said when I addressed Just Go With It, Workplace Stockholm Syndrome is a very real thing. Despite being a good 20 years younger than her boss, this girl would do anything for him and clearly felt a deep attraction for some reason or another and Uncut Gems probably would’ve landed somewhere in the middle of the rankings if I’d decided to include it.

So that’s that. As is the case with most lists like these, not everyone will agree, but it made the most sense in my head. If you’re wondering why I didn’t address Mr. Deeds, 50 First Dates, Click, or anything else that didn’t make the cut, it’s not because I necessarily thought those were realistic but because they were far more believable than all of the relationships covered above.

I know these are just movies, but if anything, I kind of hope this piece inspires you to go after the girl you never even dreamed of actually dating. Maybe it’ll work out. Maybe it won’t. If it doesn’t, you can always just did what Sandler did and spend years making a name for yourself in Hollywood before reaching a point where you can write scripts and have a hand in the casting process that at least give you a taste of what it’s like to land someone out of your league.