Out Of His League: The Women Of Adam Sandlers Movies
A few things have remained constant through Adam Sandler’s career: His films make a ton of money, he plays the same guys in nearly every movie, and he casts really hot women to play his love interests. Some of his casting choices range from believable to as likely as pigs flying. We’ll rank them all out of ten on the ‘Delusional Dating Scale’.
Bridgette Wilson (Billy Madison): 6/10 on the ‘Delusional Dating Scale’
Sandler plays the dumb, unemployed son of a hotel magnate who attempts to complete every grade of public school to show his father that he responsible enough to run the company. Bridgette Wilson plays Veronica Vaughn, his third grade teacher who has no interest in his money and is turned off by his attitude and lifestyle. Vaughn eventually comes around when she see’s that Billy is actually a nice guy with good intentions. This is a mid 90’s Sandler and Wilson does only play a 3rd grade teacher.
Julie Bowen (Happy Gilmore): 5/10 on the ‘Delusional Dating Scale’
‘Happy Gilmore’ has Sandler becoming a pro golfer who uses his unconventional swinging style to vault him to the top of the PGA rankings and into the arms of Julie Bowen. Bowen was at the top of her game in the movie but only played a PR rep. for the PGA tour. On the other hand, Sandler does play a professional athlete which helps give credibility to how he would end with Bowen by the end of the film.
Drew Barrymore (The Wedding Singer, 50 First dates and Blended): 4/10 on the ‘Delusional Dating Scale’
Drew Barrymore is the only actress that has appeared more than once as Sandler’s love interest by appearing in ‘The Weddings Singer’, ’50 First Dates’ and their recent abomination, ‘Blended’. Barrymore makes the most sense to appear as Sandler’s girlfriend since they match up the most compared to the other women that appear on this list. This movie girlfriend checks out.
Fairuza Balk (The Waterboy): 2/10 on the ‘Delusional Dating Scale’.
Fairuza Balk hooking up with Sandler in ‘The Waterboy’ matches up with Sandler perfectly as far as looks and character go. Balk and Sandler both play Louisiana red necks living on the bayou who come together after Sandler becomes a star football player for the University of Louisiana. If anything, Sandler is dating down in this one.
Joey Lauren Adams (Big Daddy): 3/10 on the ‘Delusional Dating Scale’
‘Mr. Deeds’ was Sandler’s follow-up to his stellar 1998, which saw him star in two films that grossed over $120 million and gave him Carte blanche to put whoever he wanted in his movie. Joey Lauren Adams played Sandler’s at-first reluctant girlfriend of the barely employed, failed lawyer with a massive yet dingy apartment played by Sandler. Adams does play a lawyer herself and is dating down with Sandler, but he does get his shit together by the end.
Patricia Arquette (Little Nicky): 6/10 on the ‘Delusional Dating Scale’
Be careful flipping through the channels and landing on the movie ‘Little Nicky’ because you might be mistaken and think Sandler is in a serious drama about a mentally handicapped person. Sandler’s love interest is played by Patricia Arquette who frumps herself up for the role so she matches up to Sandler’s character. Frump or no frump, she’s still Patricia Arquette and out of Sandler’s league.
Winona Ryder (Mr. Deeds): 3/10 on the ‘Delusional Dating Scale’
The plot of ‘Mr. Deeds’ would allow Sandler to date any woman he wants since he plays an average Joe who inherits billions of dollars. On the other hand, Winona Ryder plays a sleazy tabloid reporter who is using Sandler while pretending to be interested in him. She does realize that she has true feelings for him and quits her job to prove that she’s really in love with him. You win this round Sandler.
Marisa Tomei (Anger Management): 7/10 on the ‘Delusional Dating Scale’
Anger Management marked the first film that Sandler really started going off the rails in the casting choices for his girlfriend. Sandler plays an inattentive pet clothing designer that lets everyone else walk all over him while Marisa Tomei plays an aspiring poet who looks like Marisa Tomei. See the discrepancy here?
Kate Beckinsale (Click): 8/10 on the ‘Delusional Dating Scale’
The first truly egregious choice for one of Adam Sandler’s movie love interests is Kate Beckinsale in the 2007 comedy ‘Click’. You can go on and on with some song-and-dance about how he becomes really successful in the movie but at that point, even Kate Beckinsale had left him. You half expect his real wife to walk in at some point and have Beckinsale be revealed as the hot nanny that he was having an affair with. But even that wouldn’t make any sense.
Jessica Biel (I now Pronounce You Chuck & Larry): 8.5/10 on the ‘Delusional Dating Scale’
Adam Sandler ending up with Jessica Biel is a crime in and of itself even in the strange plot of ‘I Now Pronounce You Chuck & Larry’. Sandler and Kevin James ply firefighters who enter a domestic partnership and pretend to be gay so James can name his children beneficiaries to his life insurance policy. Somehow this leads to a soaking wet Biel asking Sandler to feel how her boobs are real since she thinks he’s gay ultimately leading to the two of them coming together in the end. Was this scene conceived and then an entire movie was written around it?
Salma Hayek (Grown Ups 1 & 2): 9/10 on the ‘Delusional Dating Scale’
Is there any scenario outside of Adam Sandler becoming a multi-billionare that ends with him being married to Salma Hayek? Sandler is pretty much laughing in the face of everyone by casting Hayek in the role of his wife even if his character is a high-powered Hollywood agent. Hayek’s table-top dance in ‘From Dusk Till Dawn’ has probably been watched and analyzed more times than the Zapruder film, and casting her in the role of Sandler’s wife could be the most unbelievable thing portrayed on film.
Jennifer Aniston & Brooklyn Decker (Just Go With It): 10/10 on the ‘Delusional Dating Scale’
‘Just Go With It’ centers around Adam Sandler faking a lengthy divorce with Jennifer Aniston so he can trick and ultimately land the uber-hot Brooklyn Decker. The only thing more unbelievable than Brooklyn Decker playing a sixth-grade math teacher named ‘Palmer’ is that Adam Sandler would have the slightest chance at getting with her AND Jennifer Aniston. Making casting choices like this is not only unrealistic but downright irresponsible.
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