Mainstream Monday: Ranking the Many Loves of Adam Sandler


If you think Passion of the Christ is a foreign language film…If you have no idea what an Uncle Boonmee is…If you think a Carey Mulligan is something you mark on a golf scorecard…If Domino is your favorite Quentin Tarantino movie, Mainstream Monday is the place for you! In Mainstream Monday we leave the “art” to the critics and discuss what the “other” 90% of movie fans are watching. It’s everything you love to hate about the movies. This week we’re discussing…the totally unrealistic love interests of Adam Sandler.

If you read this column regularly, you know I’m a big fan of Adam Sandler. Why the admiration? I’m not really sure, to be completely honest. He just seems to be a regular guy with a great sense of humor who worked his way up from bit roles like “Smitty” on the Cosby Show to his current standing as one of the most powerful men in Hollywood. Through all of this he’s consistently shown to be willing to be loyal to his less successful friends (*ahem* Schneider & Spade), and keeps from getting an out of control ego. Even though many of his most recent films have been less than spectacular, his fanbase continues to show up and make them successful.

While his films always have peculiar quirks to them, there is one constant that remains in them all: Sandler is a schlub who somehow fights his way into the heart of some beautiful girl. In light of this (and at risk of coming off Zuckerburgian, i.e. farm animals and such), I thought it would be fun to go back through his career and review all of the beautiful women he’s shared the screen with and, by reviewing how far out of his league they appear to be, see which matchup is the least realistic. For your reading pleasure I’ve ranked them, beginning with the matches that would have the best chance of working in real-life, all the way down to the ones that would never work, ever, ever. Obviously this all just speculation as I have no knowledge of these people outside of their film roles and public appearances. It’s a “just for fun” kind of thing. So relax and just go with it. (Dangit.) Why did I do this? The same reason you’re reading this: sheer boredom. Enjoy!

#19 Marisa Tomei Anger Management

If I was a celebrity matchmaker, I would definitely set these two up. Marisa Tomei is just cute. She’s what every guy really wants. She’s sweet and nice and funny and adorable and sugar and on top of all that she’s beautiful. And she’s another one who has managed to stay just as cute as ever through so many years on the screen. In Anger Management she helps Sandler overcome his fear of confrontation and the anger he hides below the surface. All so he can finally work up the courage to kiss her in public…..poor, poor Adam Sandler. I’m starting to hate this guy.

#18 Jennifer Aniston From the film Just Go With It

A few years ago I would have put Aniston near the bottom of this list, as Adam Sandler is anything but Brad Pitt-esque. However in recent years, whether through a change in personality or the acceptance of the effects of time, Aniston has dated a lot of guys who fall closer to the relaxed personality of Adam Sandler. (And when I say she’s dated a lot of guys, I mean she’s dated A LOT of guys) As it is now I think these two long-time friends might actually have a small chance, because she’s a truly funny person and has shown great chemistry with Sandler in interviews. Who knows what the future might hold?

#17 Courtney Cox From the film The Longest Yard

What can I say, the girl’s still got it. She was completely believable as Sandler’s hollywood wife in this shabby remake of the classic Burt Reynolds movie. She’s hot enough to get her own show about “Cougars” (although the writers have since lamented those first few plotlines and settled into a nice little ensemble comedy piece). Cox seems a lot like the characters she plays on TV - a great mom, if a bit uptight, and a generally warm person. Call me crazy but I think these two would be pretty great together.

#16 Julie Bowen From the film Happy Gilmore

Okay I have to make one caveat here: I’m thinking Julie Bowen more in her current Modern Family stint and not the half-mullet sporting Bowen from Happy Gilmore. Although if anyone can make it work, its the charming Bowen. Time has been kind to Julie as she easily holds her own next Sofia Vergara every week. Although she played the “straight guy” to Sandler’s Happy here, she showed a little spark of her own, and the two of them actually seem like they’d make the kind of couple you want to invite over for a game night. (Yes I’m old and married, leave me alone)

#15 Katie Holmes From the film Jack and Jill

Actually this one seems pretty feasible. In fact, the only thing about Jack and Jill that seems even remotely possible is the idea that a goofball like Sandler might settle down with a calm, down-to-Earth girl next door type like Katie Holmes. Although judging by who she actually settled down with, perhaps Sandler’s personality wouldn’t be….how you say…”electric” enough for her?

#14 Keri Russell From the film Bedtime Stories

I agreed with Nathan Fillion’s character in Waitress that Keri Russell looked “tragically cute” in her waitress uniform. I’m pretty sure Keri Russell would look cute in just about anything and she doesn’t disappoint here as she changes from costume to costume in Sandler’s “stories”. Keri seems to have a warm personality that would mesh well with Sandler and wouldn’t allow her to be swallowed up and forgotten in his star power.

#13 Patricia Arquette From the film Little Nicky

Now here’s a girl who lands right in Sandler’s wheelhouse. She’s not blow-you-away gorgeous like some of Sandler’s co-stars. Instead she’s just a normal girl. Arquette is a good actress who doesn’t have to rely on looks to sell a role. Unfortunately for her, many actresses with far less talent have gotten roles she deserves. Playing an awkward bag lady who’s just enough of a misfit to fall for Satan’s side-mouth-speaking son in this movie didn’t help things.

#12 Leslie Mann From the film Funny People

Leslie Mann finds herself this high on the list because she’s not only a beautiful woman, but she genuinely seems like she’d be hilarious and just generally a lot of fun to hang out with. See girls, looks aren’t everything! It also helps to be uproariously funny so…y’know…write some stand-up or something. Torn between Eric Bana and Adam Sandler isn’t even a challenge. Adam Sandler is way more desirable than Bana, right? It would appear that way in light of all the women on the list. Judging by her real-life husband (Judd Apatow), I’d say she and Sandler would work pretty well together.

#11 Winona Ryder From the film Mr. Deeds

Winona Ryder’s best feature are her big Doe eyes that somehow seem to sparkle throughout Mr. Deeds even though she is clearly aware she’s in a movie that has lost its soul. But Ryder has that small town girl next door thing working for her even in her role as a New York tabloid show reporter who falls for “new money” personified in Sandler’s Deeds. But for some reason she seems just a bit too “odd” for Sandler. Maybe it’s just me.

#10 Drew Barrymore From the film 50 First Dates & The Wedding Singer

You can’t convince me, don’t even try. Greater men and women then you have tried and failed to assure me that Drew Barrymore is hot. I’d take Hilary Swank over Barrymore any day (for you American The Office fans). The only film of hers I thought she was even cute in was Mad Love. But she has the kind of charm that would make her a fun date regardless of her looks and she’s only one of all these girls that Sandler chased twice so that earns her the 12th spot on our list. But if Ryder is “a bit too odd” then Drew is way too odd for a drama-free character like Adam Sandler. Although after Tom Green maybe she’s turned a corner similar to that of Aniston’s?

#9 Joey Lauren Adams From the film Big Daddy

I believe that somewhere in the world there is a plastic surgeon’s office, and in that office there is a wall. On that wall is a set of before and after photos. The before features Joey Lauren Adams and the after is a picture of Jennifer Tilly. Remember Joey Lauren Adams? With that cute little voice she stole her way into our hearts in several movies and even made Ben Affleck work in Chasing Amy. It’s clear from the start the only possible ending is that she will fall head over heels for Sandler. But in real life she seems like she would be way too high-maintenance for a laid-back guy like Sandler.

#8 Fairuza Balk From the film Waterboy

Guys like their women with a bit of mystery….and every once in a while just the tiniest bit of flat-out crazy. Balk walks that line perfectly as Vicki Valencourt, helping Sandler’s mama-centric waterboy break free of his mother and ‘become a man.’ But outside of the world in which Sandler plays a speech-challenged grown man working as a “water distribution engineer”, I don’t see these two meshing whatsoever. Balk seems like the kind of girl that would want a guy who is dark and brooding, an act Sandler can only sustain in his occasional foray into dramatic roles.

#7 Bridgette Wilson From the film Billy Madison

Her best look probably came in the forgotten comedy Love Stinks but in Madison we’re supposed to believe women who look like Barbie and can believably play Sonia in a Mortal Kombat movie would ever actually fall for the biggest man-child Sandler’s ever brought to the screen (and that’s saying something). In real life Wilson’s last name became Wilson-Sampras, and seeing as she went after a professional athlete, I have a hard time believing she would settle down with a schlub like Adam Sandler, no matter how funny she thought he was.

#6 Paz Vega/Tea Leoni From the film Spanglish

Spanglish is one of Sandler’s best films in my opinion. Vastly underrated, with surprising performances from an understated Sandler and an out-of-control Tea Leoni. But the real star of the show is Paz Vega. Hired to be Sandler’s housekeeper/nanny, she becomes his emotional release valve in direct contrast to his overbearing stress-inducing wife Leoni. Only in Hollywood can you find “maids” who look like Jennifer Lopez and housekeepers who look like Paz. But Paz is way out of his league beauty-wise and Tea seems like she might be as high-strung as some of her characters (including this one), so neither is a great fit for him.

#5 Emmanuelle Chiriqui From the film You Don’t Mess With The Zohan

It wasn’t that long ago that Chiriqui was playing the mysterious girl on the subway being desperately searched for by Lance Bass. That’s right you heard me, look it up. Just a few years later and she’s best known as “Sloan” from Entourage. In Zohan she seems to be the only woman in the world who can resist Sandler’s charms. But….this is an Adam Sandler movie, so this ridiculously out-of-his-league woman will at some point relent and hook up with him. In real-life I just don’t see how these two would even carry on a conversation, much less a relationship.

#4 Kate Beckinsale From the film Click

Kate Beckinsale is one of the most beautiful women alive and she is way too good for this movie. Although given her role choices of late, maybe I should reconsider that just a bit. But regardless of her career path, Kate Beckinsale is a classic Hollywood beauty. The fact that she got cast as a housewife to Sandler’s latest “everyman” is just a bit sad. In real life Kate is probably nicer than I imagine her (a particularly snooty kind of British), but regardless of her real personality these two just don’t make a great couple.

#3 Jessica Biel From the film I Now Pronounce You Chuck & Larry

Biel is just an out-of-this-world beauty and seems like fun to hang around to boot. And though her personality and relationship with a goofball like Justin Timberlake might make it appear as though she’d be a good fit for Sandler, I just think the age difference and lack of shared interests would cause an even bigger rift in the relationship than their mismatched looks. But in Chuck and Larry none of that is a problem. As if the pairing of Biel and Sandler wasn’t too difficult to accept, his character is established in the beginning by seducing a straight-laced doctor and convincing her to join in a six or seven-way (not sure just how many girls there were) with Tila Tequila and several other nameless Hooters waitresses. Totally believable.

#2 Brooklynn Decker From the film Just Go With It

She’s a supermodel married to a tennis player. I think I’ve said enough.

#1 Salma Hayek From the film Grown Ups

This is by far the biggest mis-match of the bunch. Hayek is incredibly miscast for this movie, just one of the many problems with Grown Ups. Not for a second can you actually believe that Adam Sandler, regardless of how successful his character may be, could ever get with a woman like Salma Hayek. It just could not happen. Every time I saw the two of them together on the screen I felt like I had to be watching two different movies. The two of them kissing just seemed like an abomination. Hayek is married to royalty and breastfeeds babies from third-world countries. Somehow I don’t think that would mesh too well with Sandler’s particular lifestyle.

Now it’s your turn. How would you rank ’em?


About Author

Host of Next Projection's ongoing Mainstream Monday series. I enjoy the occasional film, but most of the time I just watch movies. I'm no film student; just an old-fashioned homemade addict of cinema.

  • me

    slama hayek is one of the most beautiful women of all time…more than any or many supermodels…remeber, supermodel and beauty are not tied up…been a suoermodel doewnt mean that you are beautiful or hot…all rankings and choices of supermodels are pick by gay men…enough said.