Photo Credit: The Kobal Collection
Oh, how far Lindsay Lohan has fallen since she played cute, freckled twins in The Parent Trap and scored big-time success as the new student in Mean Girls. Wouldn't it be nice to forget about her role as a dead stripper in I Know Who Killed Me and her failed attempt at embodying Elizabeth Taylor in Liz & Dick?
Considering Lohan's countless troubles with the law, trips to rehab and problematic attitude on set, it's not exactly surprising that her reputation as a bankable star has taken a nosedive. As she prepares to enter rehab once again, can she save her career?
Before her May 2 deadline to enter a treatment facility, the actress will see the release of her latest film, Scary Movie 5 -- co-starring Charlie Sheen, who has had a troubled life of his own -- on April 12. We'll also see Lohan in Bret Easton Ellis' racy The Canyons alongside porn star James Deen (who just filmed a sex tape with Teen Mom's Farrah Abraham), though that movie has yet to receive a release date. Neither film sounds promising, but things weren't always this bad. Let's take a look back at the peaks and valleys (and giant chasms) in Lohan's once-promising film career -- from the best to the very worst.
Mean Girls (2004)
PARAMOUNT / THE KOBAL COLLECTION / GIBSON, MICHAEL
The highlight of Lohan's career was in this Tina Fey-written comedy about a young girl entering a scary new world -- the American high school -- after being home-schooled in Africa. She certainly didn't expect it to be like this: full of mean girls! Also starring Rachel McAdams, Amanda Seyfried and Lacey Chabert, this film was a huge success and is still considered as showcasing Lilo at her best.
The Parent Trap (1998)
THE KOBAL COLLECTION / RKO / SEBASTIAN, LOREY
The freckles. The red hair. The cute smile. We can never forget when we were first introduced to this adorable child star and what talent she had! Lohan played not one, but two characters, at the tender age of 12. She starred as twin sisters who are separated when their parents (Natasha Richardson and Dennis Quaid) split up; the girls try to reunite them once they find each other. While watching this film, you never once thought it wasn't real twins!
Freaky Friday (2003)
WALT DISNEY PICTURES / THE KOBAL COLLECTION / BATZDORFF, RON
In another remake, Lohan teamed up with former teen star Jamie Lee Curtis for their take on what happens when a girl and her mom switch bodies. The film was a success for Lohan; it continued to show her comedic skills and began to give her a foothold in Hollywood. It took place at a time when the young actress was also pursuing a music career, and the movie's plot even offered her a chance to sing. She actually wasn't half bad!
A Prairie Home Companion (2006)
PICTUREHOUSE / THE KOBAL COLLECTION
This was one of Lohan's first ensemble films, and also one that is still referred to by many as a favorite as Lilo grew into adulthood. Starring alongside Meryl Streep, Kevin Kline and Tommy Lee Jones, the movie got rave reviews as it brought the story of the real-life radio broadcast show to life. It also gave Lohan another chance to show off her growing singing voice and to surround herself with acting greats.
THE KOBAL COLLECTION / WEINSTEIN CO.
The star continued her run of ensemble films by snagging a role in this star-studded film about the shooting of Robert Kennedy at the Ambassador Hotel in L.A. in 1968. Anthony Hopkins, Emilio Estevez and Laurence Fishburne also starred; the actress shared her scenes mostly with Elijah Wood, playing a girl who is preparing to marry her best friend so he doesn't get sent off to the war in Vietnam. The film showed the depth of the characters Lohan was capable of portraying.
Herbie: Fully Loaded (2005)
WALT DISNEY PICTURES / THE KOBAL COLLECTION
Hoping to capitalize on her growing young audience, Lohan returned to her Disney roots in another remake. This time, she played a girl from a racing family who desperately wants to become a famous driver herself. When her dad (Michael Keaton) gives her the run-down old Beatle Herbie instead, the car takes on a life of its own. The film was moderately successful for the actress, and was the last successful run she would have with kid fare.
Confessions of a Teenage Drama Queen (2004)
WALT DISNEY PICTURES / THE KOBAL COLLECTION / KRAYCHYK, GEORGE
This film was released right after Mean Girls, but it was nowhere near as successful -- it just wasn't as smart or funny. As a girl who is forced to leave the bright lights of New York City and move to the suburbs of New Jersey, she refuses to give up on her musical-theater dreams -- no matter what it takes. Yet another movie focusing on Lohan's character as a singer in a teen world, this one fell flat.
Just My Luck (2006)
20 TH CENTURY FOX / THE KOBAL COLLECTION / WETCHER, BARRY
In an attempt to become the next Reese Witherspoon, Lohan kept trying her luck (no pun intended!) in the rom-com world with this film co-starring Chris Pine. She played a girl who has terrible luck, but in the midst of it all, meets her dream guy. With bad reviews and a lack of success at the box office, it was the last stab Lohan took at the genre.
Georgia Rule (2007)
THE KOBAL COLLECTION / UNIVERSAL PICTURES
This filming of this movie took place when the actress' personal life was really starting to spin out of control -- including constant reports that she wasn't showing up to work. One of the producers even lamented her bad behavior in a public letter. Lohan starred alongside Jane Fonda and Felicity Huffman in this drama about an estranged family rocked by a revelation Lilo's rebellious character makes.
The Kobal Collection / Twentieth Century Fox
La Lohan pulled a 180 taking a part in Robert Rodriguez's violent and gritty exploitation film. The movie's take on a fake commercial that was featured in the director's Grindhouse showcased the star in a way that we never predicted -- and in a role no one really wanted to see. Audiences watched as her character, who is kidnapped and takes part in an adult film, then rocks a nun habit and totes a machine gun as she runs from a church. Critics, however, didn't despise it.
Liz & Dick (2012)
Larry A. Thompson Productions / The Kobal Collection
Lohan hoped to use this Lifetime biopic of the famed Elizabeth Taylor as a way to stage a comeback; sadly, she failed at the attempt. Starring alongside Grant Bowler as Richard Burton, Lilo tried to embody one of the most famous women in Hollywood, but her performance turned out to be laughable. She came across as a young girl just trying to play dress-up.
I Know Who Killed Me (2007)
THE KOBAL COLLECTION / TRI-STAR / BENNETT, TRACY
Who would have thought this bright young actress would one day end up playing a stripper on the big screen? Well, it happened in this suspense thriller. Lohan is first seen as the victim of a serial killer, but then shows up with a different name, claiming she is not the woman everyone believes her to be. This film makes us wish the actress had passed on playing twins for a second time.
Inappropriate Comedy (2013)
Courtesy of Square One Entertainment
This ridiculously offensive film has been the complete bomb of Lohan's career, coming at a time when that was the last thing she needed. Co-starring, for some reason, Academy Award-winner Adrien Brody, the movie was seen by basically no one, bringing in an average of $625 per theater. Considering that it was directed by the guy behind ShamWow and SlapChop, that shouldn't be too surprising.
Rana Meyer is the Associate Entertainment Editor for iVillage. Find her on Google+.