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How Jake Gyllenhaal, Thomas Haden Church & Lindsay Lohan Were Almost In ‘The Hangover’ & More

How Jake Gyllenhaal, Thomas Haden Church & Lindsay Lohan Were Almost In 'The Hangover' & More

With “The Hangover Part III” arriving next month, and now a massive R-rated comedy franchise, it’s easy to forget that way back in 2009, this movie was not expected to be a hit. Oh sure, Warner Bros. knew it would do well (it didn’t cost them very much either), but they couldn’t have predicted how well it was going to do when arguably the biggest name in the cast was Heather Graham. Guys like Bradley Cooper and Zach Galifianakis had not taken off yet, but over $460 million worldwide later, their lives changed instantly. But what if the casting had gone a different way?

The Hollywood Reporter has put together a pretty fascinating oral history of the series, focused mostly on the first movie, but dipping into the next two installments as well, and perhaps the most interesting takeaway is who might’ve starred in the movie. “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],” Todd Phillips said. “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.”

Of course, Galifianakis did meet with Phillips and the rest is history, but the idea of Chuch in the Alan role is fascinating — it certainly would’ve been a wholly different character. Speaking of which, Heather Graham‘s Jade — the stripper with a heart of gold — was also a surprise turn for the actress who had been drifting for a while by that point. But again, it could have been someone else entirely in the role. “I did meet with Lindsay Lohan a little bit [before casting Heather Graham], and we talked,” Phillips said. “Honestly, it felt like she ended up being too young for what we were talking about. People love to attack her for everything, like: ‘Ha, she didn’t see how great The Hangover was going to be. She turned it down.’ She didn’t turn it down. She loved the script, actually. It really was an age thing.”

But all’s well that ends well and the right choices were made, and chemistry was electric. So what’s in store for the third movie then? “[It’s] a very different story. Nobody wakes up in this movie — there’s no forgotten night. But it definitely is a movie that uses what happened in the first two movies,” Phillips said. “It’s very much all one big story of [how that moment when] Alan buys drugs from Black Doug in the first movie basically fucked their lives up for six years.”

Will this new movie reach the future classic heights of “The Hangover Part II“? Only time will tell. ‘Part III’ opens on May 24th.

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