It must be nice being Adam Sandler.

You make millions of dollars to hang out with your friends on film, you can constantly dress like a toddler on a play date, and you own the production company that makes your movies so can cast hot girls as your romantic interests.

For such a low standard of comedy, it’s actually quite a genius idea. Let’s go through his career and look at the top 12 Adam Sandler love interests. These aren’t ranked by present day, just by their character in the movie.


  • 12

    Winona Ryder in 'Mr. Deeds'


    Ryder played a reporter that was trying to get the inside story on Sandler, who was the recent recipient of a fortune.

    Odds of her actually dating Sandler’s character: Moderately High. She was arrested for shoplifting so she’s known to make bad decisions.

  • 11

    Drew Barrymore in '50 First Dates' / 'The Wedding Singer'


    Barrymore pulled double duty and played his love interest as Julie Sullivan in 'The Wedding Singer' and as Lucy Whitmore in '50 First Dates.'

    Odds of her actually dating Sandler’s character: High. This is probably the only couple that makes sense. Plus, she had amnesia in '50 First Dates' so she would forget his terrible jokes at the end of every day.

  • 10

    Katie Holmes in 'Jack and Jill'


    We could have gone with Sandler in drag for this movie, but Katie Holmes seemed like a more attractive choice. Maybe it’s because of 'Dawson’s Creek', but she always felt like a celebrity you could possibly with if you asked her for a date.

    Odds of her actually dating Sandler’s character: Moderate. She seems a little too intelligent for his shenanigans, but then again maybe her character would also like to join a cult and be held hostage in her house of Scientology. This couldn’t be worse than that, right?

  • 9

    Fairuza Balk in 'The Waterboy' 


    Vicki Vallencourt was hot in a weird way. Sure she was extremely attractive, but something about her made you feel like she would steal all your silverware while you were sleeping.

    Odds of her actually dating Sandler’s character: Hopefully low but shockingly high. Clearly this is the dumbest of all the Sandler characters. I would hope she would be turned off by his lack of basic intelligence and horrible mother, but I could see her marrying him to get back at her parents.

  • 8

    Salma Hayek in 'Grown Ups'


    In the ultimate example of Sandler just hanging out with his friends on camera, 'Grown Ups' seems more like a series of excuses for his pals to party together. No perk is higher than Sandler getting to be married to Salma Hayek.

    Odds of her actually dating Sandler’s character: High. Sandler plays a high-powered Hollywood talent agent. If she were the least bit of a gold digger then this wouldn’t come as a huge surprise.

  • 7

    Joey Lauren Adams in 'Big Daddy'


    Oh man, Joey Lauren Adams was one of the highlights of the ‘90s. Between 'Dazed and Confused,' 'Mallrats,' and 'Bio-Dome,' she may have been the most underrated hottie of the decade. Here she played a successful attorney named Layla Maloney.

    Odds of her actually dating Sandler’s character: Surprisingly high then appropriately low. Sandler is a law student so I could see her getting roped in and hoping he’s going to clean up his act and become successful. However, once he adopts a kid as a stunt to impress her, you’d have to realize he’s a sociopath and get out of there.

  • 6

    Kate Beckinsale in 'Click'


    I’m not sure how you go from being a werewolf-murdering vampire in 'Underworld,' to playing the lonely housewife of Sandler, but unfortunately it happened. There’s not a single werewolf in this entire movie!

    Odds of her actually dating Sandler’s character: Please let it be low. Maybe it’s just my personal love of Kate Beckinsale, but the thought of Sandler talking in that stupid baby gibberish voice while deflowering her makes me want to eat a sword.

  • 5

    Paz Vega in 'Spanglish'


    The Spanish beauty plays an immigrant mother who is trying to provide a better life for her daughter. Unfortunately for her, she has to work for a completely dysfunctional family with Sandler and Tea Leoni constantly on the verge of murdering each other.

    Odds of her actually dating Sandler’s character: Hopefully low. He’s an unhappily married rich guy who is trying to seduce his housekeeper. It’s either going to end bad or horribly, horribly bad.

  • 4

    Emmanuelle Chriqui in 'You Don’t Mess with the Zohan'


    The 'Entourage' starlet moved to the big screen as the love interest of a military super soldier turned hairdresser. It must feel ridiculous having to play the normal person in a movie as absurd as this.

    Odds of her actually dating Sandler’s character: Moderate. He is extremely flexible, but his hair and goatee looks like a contemporary Christian music artist from 1994.

  • 3

    Bridgette Wilson in 'Billy Madison'


    Sandler plays a man-child so intellectually inept that he struggles with basic human skills. Bridgette Wilson is the abnormally attractive teacher that is trying to help a grown man learn how to write in cursive.

    Odds of her actually dating Sandler’s character:  Beyond low. We’ve all heard stories about teachers seducing students but seriously, Sandler is an adult who can’t read or write. It would be borderline immoral for her to have a relationship with him.

  • 2

    Julie Bowen in 'Happy Gilmore'


    Before she was a hot soccer mom on 'Modern Family', she was the insanely hot PGA PR director on Happy Gilmore. If you have any doubts of her being ranked this high, take a little trip to Gilmore’s Happy Place.

    Odds of her actually dating Sandler’s character: Low. It would be a huge conflict of interest seeing how he’s a psychotic golfer and she’s the public relations director. Plus, he still lives with his grandma. She knows she could do better than this.

  • 1

    TIE: Brooklyn Decker/Jennifer Aniston in 'Just Go With It'


    You’ve got to hand it to Sandler for this one. Not only did he get Jennifer Aniston to pretend to be his wife, but he also had Brooklyn Decker as a love interest! I may not like your movies, but I respect your casting choices, pal.

    Odds of them actually dating Sandler’s character: None. Zero. Not a chance. Nope. Never gonna happen. Are you kidding me?