The Parent Trap (1998)
Lohan first charmed America at the tender age of 12, when the fresh-faced redhead tackled a remake of The Parent Trap, about two girls who meet at summer camp only to find they’re long-lost twin sisters. The dual roles required a passable British accent, a killer smile, and a whole lot of that patented Disney-brand child-star moxie.
Saturday Night Live host (2004, 2005, 2006)
Remember when Lohan was delivering punchlines instead of, you know, being one? The actress hosted her first SNL in ’04 to support Mean Girls‘ release, and has returned twice since then. Of her many choice skits, the portrayal of a newly busty Hermione Granger stands out for some reason…
A Prairie Home Companion (2006)
In Robert Altman’s final bow, Lohan proved she could tackle drama as she held her own alongside heavyweights Meryl Streep, Kevin Kline, Lily Tomlin, and more.
Dakota Moss (Lindsay Lohan)
I Know Who Killed Me (2007)
Again with the dual roles, this time as a hardworking student and her separated-at-birth one-legged stripper twin. Yeah. We didn’t even include a spoiler alert there in the hopes of saving you from your own morbid curiosity. As Michael Slezak put it, ”I Know Who Killed Me is 105 minutes of your life you will never get back.”