The Hollywood Reporter has an oral history of The Hangover movies out today, and, in it, director Todd Phillips reveals some actors who were almost cast in the movie. Before any actors were hired, Paul Rudd and Jack Black both passed on the project (along with others). Lindsay Lohan was considered for the Heather Graham role and “loved the script,”” but she was deemed too young for the character. Phillips reminisced, “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 [Galifianakis]. ” Jake Gyllenhaal and Thomas Haden Church were both considered for the part of brother-in-law Alan originally. “Then we thought it’d be so much more awkward if it was an older brother who’s still at home,” Phillips concluded and landed on Zach Galifianakis, who wound up becoming a big comedy movie star as a result. The same would have happened for Jake Gyllenhaal or anyone else who was cast in the part, I’m sure.