Trivia / Lindsay Lohan

• Acting for Two: Famously as twins in both The Parent Trap and I Know Who Killed Me, and also in Freaky Friday. Dual roles were sort of Lindsay's thing for a while.
• …But I Play One on TV: The success of The Parent Trap led to many early 2000s children mistakenly thinking Lindsay had a twin. Even her Freaky Friday co-star Jamie Lee Curtis asked which twin she played when she met her.
• The Cast Show Off: Lindsay performs two of her own songs in Freaky Friday.
• Contractual Purity: Mean Girls was written to be a racy, R-rated affair with - to quote Tina Fey - "wall to wall titties". When Lindsay was cast, she was considered a family friendly actress at the time, and many of the more risque stuff was toned down. Lindsay also decided to play Cady rather than Regina, fearing that playing an Alpha Bitch would hurt her image. She also turned down an offer to do a spread in Playboy (not a nude one) because she had a Disney film coming out, and tried not to dress too skimpily in public out of fear of upsetting her younger fans. By the end of the 2000s, her public battle with substance abuse and reputation for excessive partying led to her essentially playing to how she was perceived - as a drug-addicted camera girl in Machete who has two nude scenes (although she used a body double for the topless shots) and a stripper in I Know Who Killed Me.
• Dawson Casting: Averted in her roles for Freaky Friday, Mean Girls and Confessions of a Teenage Drama Queen - as she was still a teenager. In I Know Who Killed Me however, she was twenty-one playing a teenager.
• Dyeing for Your Art: She's naturally redhead but went blonde for Machete and A Prairie Home Companion, and brunette for I Know Who Killed Me.
• Executive Meddling: Disney execs apparently found her too voluptuous for Herbie: Fully Loaded and digitally reduced her bust size.
• Fake Brit: She gives Annie James in The Parent Trap a very plummy English accent, which is quite decent. The I Am Very British tones are justified by her mother being Natasha Richardson and a well-to-do fashion designer in a very posh part of London.
• Meta Casting: By the time of her reputation as a Hard-Drinking Party Girl, she starred in several films reflecting this.
  • Machete has her as a wannabe celebrity who shoots home porn movies, even using her own mother for Girl on Girl Is Hot, and is introduced being rescued from a drug binge.
  • In I Know Who Killed Me, she plays dual roles; a Teen Genius and a long lost twin who's a down-on-her-luck stripper.
  • Georgia Rule as a promiscuous, drug-addicted teenager who gets into a car crash at the start of the film.
  • In the Lifetime movie Liz & Dick, she plays Elizabeth Taylor, another actress whose talent ended up eclipsed by her scandalous personal life.
• Real-Life Relative: Her family members cameo as extras in The Parent Trap, LifeSize, and Freaky Friday.
• Star-Derailing Role: Although her reputation as a Hard-Drinking Party Girl wasn't doing her any favours, I Know Who Killed Me seems to be the film that finally did her in. The critically trashed Lifetime Movie of the Week Liz & Dick certainly didn't help either. The film Just My Luck is regarded as the film that started the downfall - her father confessing that it was the first time she overdosed on cocaine.
• Star-Making Role: The Parent Trap got her some attention, but it wasn't until she was in her teens and the two hits of Freaky Friday and Mean Girls that she was put on the map as a superstar.
• What Could Have Been:
  • She was offered a lot of roles after the success of The Parent Trap but turned them down and didn't act for another three years - determined to have a "normal childhood" for a while.
  • As noted above, she was going to play Regina in Mean Girls, but thought playing Cady was a better option.
  • It was very close between her and Hilary Duff for the role of Anna in Freaky Friday. When she lost the role, Hilary reportedly demanded that an episode of Lizzie McGuire have a "Freaky Friday" Flip.
  • Emmy Rossum got two roles that Lindsay turned down in 2004 - The Day After Tomorrow and Poseidon.
  • Steven Soderbergh really wanted her to play the lead in Side Effects, and she auditioned several times. But producers decided that she was too risky to hire, and Blake Lively was cast. Blake then dropped out and was replaced with Rooney Mara.
  • Her character Diane did not exist in the initial drafts of Bobby. Emilio Estevez was struggling to flesh out the story and by pure coincidence met a desk clerk at a hotel who had been present on the day of the assassination. The character Diane was inspired by this woman.
  • The guys behind Machete Kills considered asking her to reprise her role as April Booth, but decided she didn't fit into the story.
  • Mara Wilson auditioned for Lindsay's dual role in The Parent Trap, but the producers of the movie felt that she was too young for the part.
  • Lohan desperately wanted her manager to allow her to audition for the role of Maria Hill in The Avengers (2012) but he refused.
• Working Title: "There Is Only One Angel In Heaven" for A Little More Personal (Raw).