“We thought it’d be so much more awkward”: Tobey Maguire’s Spider-Man Co-Star Was Strongly Considered for ‘The Hangover’ Role That Also Had Jake Gyllenhaal in the Race

"We thought it'd be so much more awkward": Tobey Maguire's Spider-Man Co-Star Was Strongly Considered for 'The Hangover' Role That Also Had Jake Gyllenhaal in the Race
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Finding the right cast is always a daunting task to accomplish, and for a film like The Hangover, it could either make or break the movie if the casting wasn’t done right. It turns out, it was indeed a nightmare of a task for Todd Phillips, but fortunately, he managed to do everything right.

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Interestingly, there were many big names considered for various roles, some of whom were either turned down by the actors themselves or were simply refused by the studio or the script eventually went a different direction. Spider-Man star Thomas Haden Church was one of them, as was Jake Gyllenhaal. It’s now crazy to think that these actors from different Spider-Man movie universes were in the running for the role that Zach Galifianakis eventually took home at the very end.

The Hangover
The Hangover

Also Read: “It really affected my speech”: Ed Helms’ Insane Idea for ‘The Hangover’ Made Him Miserable After Trying To Keep It Hidden From ‘The Office’ Co-Stars

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The Role of Alan in The Hangover Almost Went to This Spider-Man Actor

In a sit-down conversation with The Hollywood Reporter, director Todd Phillips, along with his star cast, delved into the oral history of bringing The Hangover to life from the pages, a film that eventually transformed itself into an epic R-rated billion-dollar franchise. One of the most important aspects they discussed was the casting process, which Phillips regarded as one of the most challenging stages, especially for this particular film. Despite the movie’s strong storyline and plot, it was the cast that became the main ingredient behind the film’s success. One misstep in casting and the entire movie could have easily gone down the drain.

Thomas Haden Church as Sandman in Tobey Maguire's Spider-Man
Thomas Haden Church as Sandman in Tobey Maguire’s Spider-Man

During the casting process for the iconic role of Alan in the movie, Phillips found himself torn between several strong contenders. Initially, he wanted a younger brother character who would simply tag along with the three main guys, and Jake Gyllenhaal was considered for this role. However, a creative shift led to the idea of casting an older brother, adding an extra layer of intrigue and awkwardness to the character. This brought Thomas Haden Church into the picture. As Phillips stated,

“When we were writing, we did have [other actors] in mind. Quite honestly, we were writing the brother-in-law as a younger brother they had to take along with them — like a Jonah Hill character instead of Zach [Jake Gyllenhaal also was considered]. Then we thought it’d be so much more awkward if it was an older brother who’s still at home. [Thomas Haden Church was strongly considered.] I’ve always been a huge fan of Zach [as a comedian and actor], but Zach didn’t want to come out and meet with me.”

Unfortunately, for undisclosed reasons, the casting with Church did not materialize, ultimately giving  Zach Galifianakis the chance to swoop in and nail the role.

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Also Read: “You realize we sell Joker pajamas at Target”: The Hangover Director Todd Phillips Faced Impossible Hurdles To Have His Billion-Dollar Dream Come True

How Zach Galifianakis Was Cast for the Role

Zach Galifianakis also was no easy fish to catch, as the director initially struggled to arrange a meeting with him claiming the actor didn’t want to meet with him. In response to this, the actor stated, in the same THR interview,

“That’s not true! I was in Canada, and I flew down for an audition, and I was like, “This is going to be a waste of money because I’m not good at auditions.””

It was later revealed that Galifianakis had a deep-rooted hatred for audition processes, feeling extremely uncomfortable and believing he performed poorly in such situations. Despite his discomfort, Warner Brothers insisted on a taped audition from the actor. Overcoming his fear, Galifianakis recorded his audition, and that ended up not only securing him the role but also putting him on the map.

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Zach Galifianakis at an event
Zach Galifianakis at an event

But the studio’s initial hesitation due to the actors relatively being unknown persisted, a trait which was common in The Hangover roaster, thus, they decided to slash the film’s budget significantly to avoid taking any risks. However, the film eventually made an impressive $467.5 million at the box office, despite its budget of a mere $35 million, and shocked the studio. And the rest is history!

Also Read: “You can’t skate on your looks alone”: Bradley Cooper Had Enough and Slapped His Hangover Co-star in a Hilarious Yet Awkward Interview

The Hangover is currently available on Apple TV to rent.

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Source: The Hollywood Reporter

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Written by Sampurna Banerjee

Articles Published: 760

Sampurna Banerjee, an ardent enthusiast of pop culture and movies, pours her passion into her role as a writer for FandomWire. With a penchant for Marvel, DC, and sitcoms, she has contributed over 400 articles, staying up-to-date to the entertainment industry's latest buzz. Moreover, she's penned over 300 articles for Animated Times and shared her work across several Instagram pages. Currently she is pursuing a Bachelor's degree in Computer Science from Calcutta University.