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.
With all of that in mind, let’s now take a look at some movies Adam Sandler almost starred in but didn’t, some of which were made without him and others that were never filmed at all, including a Rat Pack biopic by Martin Scorsese,  a movie that would have seen Sandler playing multiple roles - five identical siblings - a decade prior to Jack and Jill, and Quentin Tarantino’s Nazi-smashing romp Inglourious Basterds.
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. Martin Scorsese’s all-star Rat Pack biopic Dino (in development 1998)
The role: Joey Bishop
Back in 1998, Martin Scorsese was developing a biopic of the Rat Pack, centered around Dean Martin. He had his frequent collaborator Nichols Pileggi (screenwriter of GoodFellas, Casino) working on a script, and had his sights set on an impressive collection of A-listers to play Frank Sinatra and his cronies. Variety reported that Scorsese wanted Tom Hanks as Dean Martin, John Travolta as Frank Sinatra, Hugh Grant as Peter Lawford, Adam Sandler as Joey Bishop, and Jim Carrey as Jerry Lewis. No word on who he had in mind for Sammy Davis Jr.
Hanks and Travolta, amongst others, expressed interest, but production stalled when Martin Scorsese inked a deal to make Gangs of New York. He planned on returning to Dino after Gangs, but he ended up pushing it back again. Scorsese began developing a Sinatra-centric Rat Pack biopic last year, planning to cast Al Pacino and Robert DeNiro as older versions of Frank Sinatra and Dean Martin, respectively, so it looks like Tom Hanks, Adam Sandler, and company are no longer in the mix for this one.
3. The Five Johnsons (in development 2000)
A decade prior to Jack and Jill, Adam Sandler was developing a different project where he’d be playing multiple characters who are siblings – but in this one, he’d have played five brothers. The Five Johnsons (a.k.a The Five Joes and The Johnson Five) revolved around “five identical brothers who are separated at a young age and then reunite to cause one brother misery.†This was supposed to be Sandler’s first project after Little Nicky, but it ended up falling apart before production began; however, it looks like Sandler hung onto the idea and reworked it a little bit to make Jack and Jill years later.
4. Wild Pitch (in development 2002)
Eddie Klep was the first white man to play baseball in the Negro Leagues, breaking baseball’s other color barrier in 1946, a year before Jackie Robinson became the first black man in Major League Baseball. Denis Leary bought the rights to Eddie Klep’s story in 1999 as a starring vehicle for himself but never got around to making the movie. In 2002, Adam Sandler signed on to star in a film based on Klep’s life called Wild Pitch, but this one never got off the ground either.
5. 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 Jailbabe.com. It’s pretty shocking that, after nearly 10 years, there still hasn’t been a movie called Jailbabe.com.
6. 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.
7. Fletch Won (2003)
The role: Irwin “Fletch†Fletcher
Kevin Smith originally wanted Jason Lee to star in his update of the Fletch franchise, based on Gregory Mcdonald’s series of comedic mystery novels that Chevy Chase popularized in a pair of 1980s films. The studio didn’t think Lee was a big enough star at the time, so they pressured Smith to pick a new Fletch. His shortlist in 2003 consisted of Ben Affleck, Jimmy Fallon, Brad Pitt, Adam Sandler, and Will Smith (no relation). Kevin Smith picked Affleck but then both of them dropped out. Fletch was almost played by Zach Braff then Joshua Jackson, but this long-gestating reboot seems to be shelved for now.
For more info on the numerous attempts to update Fletch over the past 15 years, check another piece I wrote, The Lost Roles of the Unproduced Fletch Reboot.
8. 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.
9. 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.
10. 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.â€
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).
11. 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!
Other unrealized projects:
Bradford Evans is a writer living in Los Angeles.