Back in 2008-2009 Lindsay Lohan had already finished with her teenage chick flick movies and was signing up for more serious and mature projects such as I Know Who Killed Me and Labor Pains. That doesn’t mean she always made wise decisions.
When the team of professionals behind the blockbuster The Hangover started casting for the film, they considered Lindsay Lohan for the role of Jade. Lohan had already played a provocative stripper in a previous project and her agent reportedly tried really hard to convince the director Todd Phillips to offer Lohan the role. When Phillips finally agreed, all that was left to do was to get Lohan to show up. Unfortunately for her, she decided to turn down the role of Jade. The 27 year old actress thought there was no potential in the screenplay. Little did she know that the movie would become a huge franchise in the near future.
Lohan probably regretted her decision afterwards, but the role had already been given to Heather Graham.