- Alexandra Owens, Titanic, 1996.
- Michelle Trachtenberg, Inspector Gadget, 1999. Refused. Made her name in three Disney movies: The Parent Trap, 1998, Freaky Friday, 2003, Herbie Fully Loaded, 2005. “ I want to act and direct like Jodie Foster” said the also gay Lohan.
- Jena Malone, Life As A House, 2000. Director Irwin Winkler like Lohan but finally felt she was too young – at 14 – for Alyssa Beck.
- Halle Bailey, The Little Mermaid, 2021. Uma Thurman’s daughter Maya Hawk, Jane Levy, Lindsay Lohan, and TV’s Zendaya were leaders of the pack vying for the titular Ariel as Disney continued struggling with diversity casting. Tragically, the early release of the caused a b(l)acklash from the usual racists farting on anti-social media about the choice of the exquisite Bailey.. The Covid 19 pandemic delayed the release until 2023,
- Emmy Rossum, The Day After Tomorrow, 2002. First of two successive films passed by Lohan to Rossum. “At the rate we’re polluting the environment and burning fossil fuels, the ice caps will soon disappear.,” said Dennis Quaid, playing his first… paleoclimatologist.
- Rachel McAdams, Mean Girls, 2004. Refused the “alpha Plastic” role of Regina George – as her fans would perceive her as arrogant. Became Cady Heron instead, smartest of the high school girls. invited into the A-list girl clique at her school – The Plastics. (Well, they’re so close to Barbie). This was the first movie script by Tina Fey, based on the lessons of Rosalind Wiseman’s non-fiction hit (wait for it): Queen Bees and Wannabes: Helping Your Daughter Survive Cliques, Gossip, Boyfriends, and Other Realities of Adolescence.
- Bijou Phillips, Havoc, 2004. “I got this one script where this girl wants to join a Latino gang and she gets raped,” recalled LL. “I can’t be doing that right now. I don’t think that’s appropriate.”
- Emmy Rossum, Poseidon, 2005. Somehow LL was first choice for Jennifer. The distinction did not impress her.
- Keri Russell, Mission: Impossible III, 2005. When Tom Cruise postponed everything to make Spielberg’s War of the Worlds, Scarlett jumped into two successive Woody Allen films, among other movies. The role of Lindsay Farris was then aimed at Lohan, Jessica Alba, Elisha Cuthbert… and Katie Holmes who won Cruise instead. (They wed in 2006). Finally, Russell was selected. Easily. She headlined the new M:I auteur JJ Abram’s TV series, Felicity, 1998-2002.
- Mary Elizabeth Winstead, Live Free or Die Hard, 2006. The two tabloid stars, Lindsay and Britney Spears, were discussed for John McClane’s daughter, Lucy. Too much baggage – and it got worse.
- Sienna Miller, Factory Girl, 2005. Lohan was, perhaps inevitably, an early choice for the biopic about Edie Sedwick, drug addict, kleptomaniac, celebutante, mental patient and Andy Warhol “supertstar.” LL tested but the producers felt she was wrong for the role. For any rôle… said the producers who called LL: “Hell! Hell!”
- Adrianne Palicki, Friday Night Lights, TV, 2006-2011. Another bright move… LL passed on Tyra Collette in 2005, because she was more keen on movies. That was before she discovered movies weren’t keen on her. And her baggage.
- Leighton Meester, Gossip Girl, TV, 2007-2008. Back in the day, Josh Schwartz wrote it as a movie – for Lindsay as Blair Waldorf, queen of her Upper East Side private school. Worked better as a CBS series where each chapter’s title was a movie pun. The Blair Bitch Project, Gone With The Will, It’s a Wonderful Lie, The Wild Brunch.
- Sienna Miller, The Edge of Love, 2007. First (bad) choice for Welsh poet Dylan Thomas’ wife, Caitlin – scripted by Sharman Macdonald for her daughter, Keira Knightley. (She preferred Dylan’s other lover, Vera Phillips – grandmother of her producer, Rebekah Gilbertson.
- Kelly Reilly, Me and Orson Welles, 2007. LL was about to sign on as Muriel Brassler when no insurance company would cover her due to her legal hassles. Lohan remains the one and only actress to have her breasts reduced rather than enlarged on a poster – and partially hidden by the title, Herbie Unloaded, in 2005. By Disney, of course.
- Jessica Alba, Bill, 2007. Working on director Robert Altman’s final film, A Prairie Home Companion, went to the troubled teen’s head. She quit this assignment because the 19-year-old felt her first-time directors (Bernie Goldmann, Melisa Wallack) were unknown and from here on, she would besticking to big name film-makers, only – OK? Yeah, like the disaster callled I Know Who Killed Me, 2007 – winner of the most Razzie awards (eight), including Worst Picture.
- Zooey Deschanel, Gospel According To Janis, 2008. Best out of the Janis Joplin biopic as Lohan seemed hellbent on achieving the same booze andheroin climax for herself.
- Bryce Dallas Howard, The Loss of a Teardrop Diamond, 2008. The eternal First Reserve… Ron Howard’s daughter made a whole career of replacing others… Kirsten Dunst in The Village, 2004. Nicole Kidman, Manderlay, 2005; Clare Danes, Terminator Salvation, 2009; Rachelle Lefevre in The Twilight Saga: Eclipse, 2009.
- Sarah Michelle Gellar, Veronika Decides To Die, 2008. Lohan agreed to play the suicidal Veronika in 2006 – until preferring smaller, independent movies to bolster attempts to be seen as a serious actress… as opposed to tabloid fodder.
- Isla Fisher, Confessions of a Shopaholic, 2008. For once, the prerequisite outsider won as Disney chose an unknown (cheaper, sure, but hilarious) after seeing everyone from the Jessicas (Alba and Biel) to Lohan (!) and Reese Witherspoon, who rigfhtly felt Rebecca Bloomwood was too close to her Elle Woods creation in the two Legally Blonde films. Also in the mix: Emily Blunt, Kirsten Dunst, Anne Hathaway, Katie Holmes, Rachel McAdams, Amanda Seyfried.
- Heather Graham, The Hangover, 2008. Convinced that the film would die at the box-office, Lohan refused to play the stripper called Jade. She soon regretted missing exactly what her failing career required – a triumph.
- Melissa George, Triangle, 2008. Wisely avoided the oddly titled Australian thriller, a supernatural Groundhog Day… at sea.
- Jessica Biel, Accidental Love, 2008. Change of waitress geting a nail in her head, leading her to Washington and to everything that was far better in HealtH, 1980. But then director Stephen Greene isn’t Altman. He is, in fact, David O Russell, changing his credit after the financial mess of Capitol Films ruined everything. By the time what started as Nailed opened in 2015, the 44th US President’s Obamacare had begun, making the focus of the “satire” meaningless.
- Mia Wasikowska, Alice In Wonderland, 2009. Her campaign for the role of Alice was not helped by headlines about her relationship with Samantha Ronson. “If people would just leave my personal life alone – because it’s really not that interesting – then I could land a great role. But all the sicko fans and the noise is so distracting.” Director Tim Burton chose the three-years-younger Australian and her gravity – so brilliantly revealed in the psychological In Treatment TV series, 2009.
- Olivia Thirlby, The Other Side, 2009. Dumped! The money men were convinced she was no longer bankable.Katie Holmes was called up but couldn’t play her due to her Broadway date with All My Sons.
- Gemma Arterton, Wuthering Heights, 2009. When Natalie Portman pulled out, Lindsay tried hard to persuade any and everyone but no one was buying her as the 15th screen version of Catherine Earnshaw.
- Kristen Bell, Burlesque, 2009. Considered for Nikki. in Cher’s first – and last – musical. So was Jessica Biel.