A Look Back at Lindsay Lohan’s Diverse Career

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Lindsay Lohan as Hallie and Annie Parker in The Parent Trap (1998)

Adorable 11-year-old Lohan's biggest gig before her feature film debut had been a one-year stint as Alli Fowler on the daytime soap Another World. It's not hard to see how she wowed casting directors after auditioning for twins Hallie and Annie Parker in The Parent Trap. She flawlessly played both twins—including speaking in a British accent as Annie—who tried to reunite her stubborn yet lovable divorced parents. Lohan won a Young Artist Award for her performance and a star was born.

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Freshman Year, Cold Spring Harbor High School, Cold Spring Harbor, NY (2001)

A fresh-faced Lohan poses for her freshman year yearbook photo at Cold Spring Harbor High School in New York. Before the paparazzi, rumors, drama and arrests, Lohan was just a normal kid who played on the school's basketball and soccer teams.

Lindsay Lohan—Cold Spring Harbor High School (2001)

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Cold Spring Harbor High School Basketball Team (2001)

A young, athletic Lohan poses with her basketball teammates back in 2001.

Lindsay Lohan Cold Spring Harbor High School Homecoming Dance

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Cold Spring Harbor High School Homecoming Dance (2001)

Lindsay and her high school buds pose for a quick pic at their Homecoming dance. Oh that we could freeze this moment in time and convince Lindsay that Homecoming is way more awesome than partying it up in Hollywood.

Lindsay Lohan as Anna Coleman in Freaky Friday

Walt Disney Co./Everett Collection

As Anna Coleman in Freaky Friday (2003)

After her success in The Parent Trap, Lohan scored a three-picture deal with Disney. One of the three movies was the hugely successful reboot of Freaky Friday. Lohan played Anna who switches bodies with her mom (played by Jamie Lee Curtis) after crossing paths with an enchanted fortune cookie. Chaos ensues, and Lohan's star continues to rise.

Lindsay Lohan as Cady Heron in Mean Girls

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As Cady Heron in Mean Girls (2004)

Lohan got to show off a different side to her acting skills in the Tina Fey penned Mean Girls. Playing a fish-out-of-water transfer student (from Africa!), Lohan had the definition of "girl next door" charm, beauty and likability that thrust her to superstar status. We loved watching Cady navigate being the new girl in school, trying to find her true friends and maybe a little romance, while avoiding the shark-like mean girl group, "The Plastics".

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Lindsay Lohan and Wilmer Valderrama (2004)

Ah, first love. The glow! The excitement! The terrible, soul-crushing rejection when it ends! Lohan and her first Hollywood love, Wilmer Valderrama, hooked up in 2004, with Lindsay even making a guest appearance on his sitcom That '70s Show. The pair split ways later the same year, which Vanity Fair said contributed to her "un-Disney-like" behavior while filming Herbie: Fully Loaded.

Lindsay Lohan New Years' Eve Times Square 2004

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Performing at the New Years' Eve party in Times Square (2004)

Lindsay bursts into the pop music scene with her first album Speak, which peaked at the No. 4 spot on the Billboard 200. She followed it up with the less successful A Little More Personal (Raw) in 2005.

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Arriving at the Vanity Fair Oscar Party (2006)

Lohan shows off her budding fashionista side at the Vanity Fair Oscar party with this gorgeous Old-Hollywood-style gown.

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Attending the Metropolitan Museum of Art Costume Institute Benefit Gala (2007)

Regardless of her trouble in the press, Lindsay continues to light up red carpet events in stunning gowns like this one at the Costume Institute Ball.

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Attending the Charlotte Ronson Spring 2009 Fashion Show with Girlfriend DJ Samantha Ronson (2008)

The relationship that launched a million tabloid stories: Lohan stuns Hollywood by stepping out with a new love, DJ Samantha Ronson. The pair had a famously tumultuous relationship (and were on-again, off-again) from 2008-2009.

Starring as April in Machete (2010)

Due to Lohan's DUI arrests, stints in rehab and jail, the actress hasn't worked consistently in the past few years. Her most recent notable role was as April in Robert Rodriguez's Machete. We feel like Lohan got into her character by picturing the ever intrusive paparazzi at the other end of that ginormous gun.

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Posing at the Giuseppe Zanotti Design Store Opening (2011)

At 25, Lohan was serving time under house arrest after being charged with a felony grand theft (later reduced to a misdemeanor) involving the theft of a $2500 necklace from a Venice jewelry store.

IFC Films

As Tara in The Canyons (2013)

Lindsay Lohan's 2012 was filled with minor parts in films like Scary Movie 5 and television shows like Glee and Anger Management. Her biggest role was channeling Elizabeth Taylor in Lifetime's Liz & Dick, which received scathing reviews. In 2013, Lohan played Tara in Paul Scrader's critically panned The Canyons. While the film wasn't well-received, Lohan's performance received critical praise. The New Yorker's Richard Brody called Lohan's performance as "electrifyingly alive; the convergence of performer and person is wondrous."

Lohan completed rehab and has been spotted looking healthy and happy. She guest starred in the series finale of the HBO comedy Eastbound & Down. She'll next take the stage in David Mamet's Speed-the-Plow on London's West End.