9 Movies Lindsay Lohan Was Supposed To Star In

Looking back at the career that could've been.

1. Gossip Girl

The CW

Years before the popular book series became a television show, Lindsay Lohan was set to star as Blair Waldorf in a movie adaptation written by Gilmore Girls-creator Amy Sherman-Palladino. The film fell apart when Amy moved on to another project. However, it was probably for the best because we all know Lindsay is really more of a Serena.

2. I Dream of Jeannie

Sony Pictures Television

This one hurts. Back when Lindsay was Disney's go-to girl for family-friendly remakes, she was set to star in an updated version of I Dream of Jeannie. While it's unclear why the movie didn't get made, it is clear that we missed out on something delightful.

3. The Hangover

Warner Bros.

Director Todd Phillips originally auditioned Lindsay for Heather Graham's role before deciding she was too young to play the part of a single-parent stripper. Clearly, he never saw I Know Who Killed Me.

4. Untitled Nick Cannon-Lindsay Lohan Romantic Comedy

Getty Images / Terry Richardson

In 2006, Lindsay was supposed to join Nick Cannon in an Adam Sandler-produced comedy about a fashion-savvy New Yorker who befriends a blind man. Nick told MTV News he thought the film would make them the next Tom Hanks and Meg Ryan. Unfortunately, the film never got made and we were never able to experience to golden age of the Cannon-Lohan RomCom.

5. The Edge of Love

Capitol Films / B. Jaye

Lindsay and her British accent were set to star opposite Keira Knightley in the vaguely sapphic period drama before they were replaced by Sienna Miller for insurance reasons.

6. Poor Things

Alberto E. Rodriguez (Getty) / 20th Century Fox Television / Jason Merritt (Getty) / Kevin Mazur (Getty)

Shirley MacLaine, Rosario Dawson and Channing Tatum were supposed to star alongside Lindsay in this canned comedy about granny gangs. Despite having all the elements of a cult classic, production was halted when Lindsay went to rehab for a second time.

7. Inferno: The Linda Lovelace Story

Tyler Shields

Hoping to cash in on her good-girl-gone-bad reputation, director Matthew Wilder cast Lindsay as Linda Lovelace in this Black List-approved biopic. She was replaced by Malin Ackerman, however, after her bad-girl antics caused almost a year of production delays.

8. Gotti: Three Generations

Jemal Countess (Getty)

While Lindsay showed up to the Gotti: Three Generations press conference in some seriously convincing Victoria Gotti drag, she was dropped from the project less than a week later.

9. Mean Girls

Paramount Pictures

In some alternate universe, Rachel McAdams bursts on to the scene as good girl Cady Heron and Regina George is the role that turns Lindsay into a superstar. The actresses had originally auditioned for each other's roles but Lindsay accepted the role of Cady after her team convinced her it would be a smarter career move.