ByJordan Morgan, writer at
Indie Filmmaker, Creator of "Rush Boogie" and please love me
Jordan Morgan

According to Splitsider, Saturday Night Live has been known for being a movie star factory ever since original cast members Chevy Chase and John Belushi each made a smooth and triumphant transition to film stardom in 1978, but perhaps no ex-SNL star has had a longer run as a major box office draw than Adam Sandler. Sure, his movies are often the subject of critical scorn, but Sandler has proven he can consistently attract large audiences to see them. He may just be the biggest movie star – in terms of box office earnings – that SNL has ever churned out. That’s no small feat, considering that the show’s alumni include major movie stars like Will Ferrell, Eddie Murphy, and Bill Murray. Sandler is also a loyal friend, using his clout to secure writing, directing, and acting gigs for his buddies. Plus, he’s successfully pulled off the comedy-to-drama transition that eludes many of his fellow funnymen. Although more dramatic turns in Punch-Drunk Love and Funny People didn’t make a ton of cash like Sandler’s biggest comedies, his performances in these films did earn him his fair share of critical praise and awards attention.

1. Very Bad Things (1998)

The role: Michael Berkow

Who got it: Jeremy Piven

Adam Sandler was attached to be a part of the ensemble, which also included Christian Slater, Cameron Diaz, and Jon Favreau, in director Peter Berg’s pitch–black comedy Very Bad Things, but he dropped out to make The Waterboy instead. Waterboy ended up being Sandler’s biggest hit to date, and it probably served his career well to skip Very Bad Things, a movie that had dim commercial prospects; however, it would have been nice to see the guy branch out a little bit by starring in a bleak, dark comedy like this one as opposed to his usual slapsticky fare.

2. Bringing Down the House (2003)

The role: Peter Sanderson

Who got it: Steve Martin

The guy who wrote the Steve Martin/Queen Latifah vehicle Bringing Down the House had Adam Sandler and Angelina Jolie in mind for the leads when he first wrote the script, which was originally entitled It’s pretty shocking that, after nearly 10 years, there still hasn’t been a movie called

3. The Hebrew Hammer (2003)

The role: Mordechai Jefferson Carver

Who got it: Adam Goldberg

From 2002 to 2003, Comedy Central made a short-lived push attempt at producing original films. In addition to such gems as Porn ‘n Chicken and Knee High P.I., Comedy Central’s push towards original films also gave us The Hebrew Hammer, a riff on blaxploitation movies that starred Adam Goldberg as a Jewish crimefighter tasked with saving Hanukkah from Santa Claus’s evil son (Andy Dick) who wants to destroy the holiday. Goldberg only won the part after Adam Sandler, Ben Stiller, and David Schwimmer all turned it down. I’m guessing that a Sandler or Stiller version of this would have made it to theaters instead of airing on Comedy Central, sandwiched between episodes of Crank Yankers.

4. Collateral (2004)

The role: Max

Who got it: Jamie Foxx

Adam Sandler was in talks to star opposite Tom Cruise in Michael Mann’s crime thriller Collateral, about a contract killer who takes a cab driver hostage. Mann ended up choosing Jamie Foxx instead, who had more dramatic experience than Sandler.

5. Charlie and the Chocolate Factory (2005)

The role: Willy Wonka

Who got it: Johnny Depp

A new adaptation of Roald Dahl’s beloved kids’ novel Charlie and the Chocolate Factory had been in development since the late 90s, with a number of candidates being up for the job at one point or another, including Jim Carrey, Adam Sandler, Nicolas Cage, Brad Pitt, and Will Smith, amongst others. Hot on the heels of Pirates of the Caribbean achieving blockbuster status, Johnny Depp scored the part, reuniting the actor with frequent collaborator Tim Burton.

6. Inglourious Basterds (2009)

The role: Sgt. Donny Donowitz

Who got it: Eli Roth

Quentin Tarantino and Adam Sandler had been talking about making Inglourious Basterds together for several years, but when the movie finally made it into production, Sandler had to pass because he was already committed to making Funny People with Judd Apatow. Sandler explained the situation in 2008:

“I read the script, it’s fantastic. But I’m shooting at the very same time. I won’t be able to do it. I’m doing a movie with Judd Apatow at the same time so that’s not going to happen, but I did read it. It is awesome…it’s definitely disappointing. I’d love to do it, but I just can’t.”

Fun fact, others who Tarantino tried to get to star in Basterds include Leonardo DiCaprio as Hans Landa (the role that went to Christoph Waltz), Simon Pegg or Tim Roth as Lt. Archie Hicox (which went to Michael Fassbender), Michael Madsen as Babe Buchinsky (a character who didn’t make the final cut of the movie), Nastassja Kinski as Bridget von Hammersmark (which went to Diane Kruger), and Eddie Murphy, presumably as Marcel, the movie’s only black character (who was played by Jacky Ido).

and finally

Knight and Day (2010)

The role: Roy Miller

Who got it: Tom Cruise

The Tom Cruise/Cameron Diaz action comedy Knight and Day spent five years in development, going through a slew of actors, directors, and titles before the studio settled on all of the elements of the final products. The original script, called All New Enemies, was a serious thriller written in 2004, but it was turned into a romantic action-comedy and retitled Wichita in 2007 when Adam Sandler signed on. Sandler dropped out, saying

“I just don’t see me with a gun”

and was replaced by Chris Tucker, with Eva Mendes signing on for the female lead and the movie being retitled Trouble Man. In 2009, Gerard Butler and Cameron Diaz joined the project, only for Butler to drop out and be replaced by Tom Cruise. And that’s how cinema history was made!

That's all folks

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