5 Iconic Lindsay Lohan Performances (And One We’d like To Forget)

We’ve officially entered the Lohanaissance Era.

After over a decade of false starts, career detours, delayed personal development, and rapturous beach club dancing, Lindsay Lohan has conquered her demons and recovered her film career. Freakier Friday, which reunites Lohan with on-screen mom Jamie Lee Curtis, has notched an even bigger opening than the original Freaky Friday. Her three recent holiday movies with Netflix have played well with both critics and audiences. She’s a wife, mother, the sister everybody would want, the friend that everybody deserves. She’s an icon, she’s a legend, she is the moment. She’s happily sober.

She’s also the sum of her parts, so to that end, let’s revisit Li-Lo’s five best performances from pop culture history (plus one that should be purged from cinematic history).

The Five Best Lindsay Lohan Performances

Anna Coleman in Freakier Friday

Freakier Friday isn’t just a box office success for Lohan. It’s also a triumphant return to the big screen, as well as definitive proof that she still has that It Factor. In the first Freaky Friday, Lohan presented herself as a promising young star with both comic timing and an ability to draw in an audience. She demonstrates both talents here while believably playing a teenager trapped in an adult’s body. She’s funny, consistent, and, despite some stultifying effects of Botox, expressive. Dear Aging Millennial Gods, please give us more movies like Freakier Friday!

Cady Heron in Mean Girls

This one’s a no-brainer! How can we list Lohan’s best performances without mentioning Mean Girls? She’s the emotional anchor of the film. She’s the anti-Regina until she’s Regina. She’s one of the O.G. straight allies in mainstream cinema. Who else do you think of when it’s October 3? Certainly not chlamydia! 

Hallie Parker and Annie James in The Parent Trap

Trap put Lohan on the map. It was the first time she’d play twins on camera, and the last time she’d ever do it well. Her dual performances were so charming that critics declared her the best part of the film. That earns it an instant mention! 

Lola Johnson in A Prairie Home Companion

It’s a shame that Lohan’s performance in 2006’s Prairie Home Companion was overshadowed by her off-screen shenanigans. This movie came right after her Oscar-considered turn in Herbie: Fully Loaded, a family film about a talking car; Herbie was mere window dressing for her newfound habit of partying. Still, Prairie gave Lohan the chance to hold her own against Meryl Streep, proving her dramatic chops in the process. Lohan never took advantage of the second chance that this movie gave her, but she did make the movie sparkle.

Avery in Our Little Secret

It is unlikely that Li-Lo’s Netflix holiday catalogue will ever appear in AFI’s 100 Years…100 Movies, but Our Little Secret is still a step above similar holiday fare. That’s mostly due to Lohan, whose performance bonafides are apparent whether she’s sparring with Kristin Chenoweth or acting stoned during a church scene. People scoffed when Netflix first announced its partnership with Lohan, but the world now has three solidly charming holiday films, and all because Lohan gave them her all. 

The One We’d Like To Forget

Aubrey Fleming and Dakota Moss in I Know Who Killed Me

2007’s I Know Who Killed Me hit theaters just as Lohan’s substance abuse problems reared their head. That said, she couldn’t have saved this movie even if she’d brought her A game. As Aubrey/Dakota, Li-Lo was required to inhabit two delusional twins, one of whom was a one-legged stripper. The movie was meant to show that she was “grown up” after Mean Girls and Freaky Friday, but was too much of a slog and mostly just made her seem like a delusional stripper.

Bonus performance we’re on the fence about: Tara in The Canyons

One of the most important historical documents of our time is this New York Times piece about the making of The Canyons. In addition to hailing from a time when most Americans still trusted journalists to deliver factual, intelligent stories about our world, it also perfectly captured the madness that Lindsay Lohan brought to the set of the movie. Sometimes she showed up late and hungover, blocking “imaginary sunlight” with her shades; other times, she delivered Oscar-winning acting. But did the movie itself, a softcore adult film dressed as arthouse fare, elevate her performance to high art? The limit to our speculation does not exist. Maybe, one day, Lohan’s turn as Tara will be considered camp or even underrated brilliance. For now, we can just hope for a sequel to The Parent Trap.