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Lindsay Lohan is a pop-culture icon who has appeared in several enduringly popular movies. From Confessions of a Teenage Drama Queen to Georgia Rule, Lohan definitely impacted the entertainment world – while her succession of tabloid headlines throughout the early 2000s ensured that her name was always forefront of the cultural conversation. While Lohan has acted in several comedies, there’s one hit that she missed out on – the 2009 comedy flick The Hangover. The film’s director later opened up about the role that Lohan tried out for, admitting that she didn’t get the part due to one specific reason.

Why didn’t Lindsay Lohan land a role in ‘The Hangover’?

Lindsay Lohan at 2019 Derby Day at the Flemington Racecourse in Melbourne, Australia
Lindsay Lohan at 2019 Derby Day | Sam Tabone/WireImage via Getty Images

In 2009, Lindsay Lohan was still one of the biggest names in Hollywood. Fresh from roles in movies like Bobby, Chapter 27, and Just My Luck, Lohan had earned acclaim for her acting range and ability to nail both dramatic and comedic roles. Still, her legal troubles and notorious hard-partying lifestyle had caused her to earn quite a reputation around Hollywood, with many deeming Lohan difficult to work with.

However, when Lohan entered into talks for a featured role in The Hangover, it was an entirely different reason that caused director Todd Phillips to go with a different performer. According to People Magazine, Phillips revealed, “Honestly, it felt like she ended up being too young for what we were talking about.” The director went on to note, “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.”

‘The Hangover’ became a breakout comedy hit

At the time that Lindsay Lohan was speaking to Todd Phillips about the role in The Hangover, the actor was only about 20 years old. Ultimately, the role of the seasoned stripper named Jade went to Heather Graham, who was close to 40 when she was cast. The Hangover, of course, went on to become one of the year’s breakout hits, with millions of fans heading to the theaters to see the comedy stylings of Phillips and his cast of talented stars, including Bradley Cooper, Ed Helms, and Zach Galifianakis.

The film spawned multiple sequels, including one in 2011 and one in 2013. While neither of the sequel films captured the lightning-in-a-bottle aspect of the original, they were still box-office successes. To this day, The Hangover is regarded as a major comedy classic.

Lindsay Lohan is making a career resurgence


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Not long after Lindsay Lohan was passed over for a role in The Hangover, the actor left Hollywood entirely. In 2014, Lohan settled in Dubai, where she started focusing on other businesses, including opening a series of nightclubs rather than acting roles. Lohan later admitted that she appreciated Dubai’s low-key atmosphere and relished the chance to live out of the spotlight for a while. 

In early 2022, Lohan signed a lucrative new deal with Netflix that will see the star getting leading roles in several original new films. Her comeback is well on the way, with her first film from the Netflix deal hitting the streaming platform in late 2022. While it’s unclear just how critics and fans will receive Lohan’s comeback, it is certain that everyone will be tuning in to see how the beloved star will handle the spotlight and the renewed media attention.