Casting What-Ifs
Lindsay Lohan nearly cast as Jade but judged too young by Phillips; Jack Black turned down Alan; Paul Rudd turned down Phil; Jeremy Piven turned down Stu; Mike Tyson refused until he learned Phillips made Old School; Alan was written as a Jonah Hill-type younger brother and Thomas Hayden Church (as transcribed) was considered
In the discussion (9)
Approx. transcript time · 00:48:10Read transcript
- Lindsay Lohan was almost cast as Jade; Phillips decided she was too young and is adamant about it, while Lohan's version is that she turned it down and it was the biggest regret of her career.
- Lohan in the movie would have felt very 2009 and not a good version of her; Heather Graham is perfect, and being a little older makes the part work better.
- One host is not as much of a believer in the theory that Lohan was a great Goldie Hawn-esque movie star whose talent was frittered away. — Sean Fennessey
- The reaction is 'Oh, how dare you?' and 'This is your worst take you've ever had', with Parent Trap offered as proof: she plays two people, one with an English accent, like a 17-year-old Meryl Streep in training; Freaky Friday is weaker.
- The Heather Graham conversation runs License to Drive, Twins, Drugstore Cowboy, Six Degrees of Separation and Swingers, by which point one host was in love, then Austin Powers; she may have been his number one 90s crush, Ed Burns dated her, and Boogie Nights, Even Cowgirls Got the Blues, Diggstown, Mrs. Parker and the Vicious Circle, Scream 2, Two Girls and a Guy and Bowfinger show she was always in good stuff and good at sending up her persona; another gets her confused with Terry Polo.
- Her ABC show Emily's Reasons Why Not never worked; Grey's Anatomy is raised as a show she might have led, but she is a comic actress who thrives in comedy; she is good here and way better than Lohan would have been, her 35 making more sense than weird 25-year-old energy.
- Jack Black turned down Alan, thank God, since he would have overpowered the other three; Paul Rudd turned down Phil and would have been doing Brian Fantana and Sex Panther while making fun of it, whereas you believe Cooper as a shit bag even greeting his wife at the wedding; Rudd has not played a guy like that outside Neil LeBute (as transcribed) plays.
- Jeremy Piven turned down Stu, thank God, probably because he was at the height of Ari Gold; Stu is the third lead.
- Mike Tyson refused to appear and changed his mind on learning Phillips directed Old School; the Galifianakis character was written as a younger brother-in-law of the Jonah Hill type until Phillips realized an older brother was funnier, and Thomas Hayden Church (as transcribed) was the other option, a different movie.