Throwback!See A Complete Guide To The Highs And Lows Of Lindsay Lohan’s Film Career

‘The Parent Trap’ (1998)

What It’s About: Identical twins Annie and Hallie, separated at birth and each raised by one of their biological parents, later discover each other for the first time at summer camp and make a plan to bring their long-separated parents back together.

Behind-the-Scenes: At the time of the film’s release, Lindsay was featured in a promotional video interview where she was asked what it was like to create two different characters in the same movie. “Well,” she said, “I just thought about how calm one was and how cool and ready to hang out the other one was.” As for her reaction to being cast in this movie, she recalled, “Oh my gosh, I started jumping up and down on the bed in my hotel room and was freaking out. I called all my friends and everything; it was so exciting, because I didn’t think it would happen.”

‘Freaky Friday’ (2003)

What It’s About: Jamie Lee Curtis is the mom, Lindsay the daughter, neither of whom get along with the other — until they literally experience what it’s like to see life from the other’s point of view when they switch bodies.

Behind-the-Scenes: Between The Parent Trap and Freaky Friday, Lindsay appeared in a pair of Disney Channel TV movies, focused on trying to live a bit of a normal life after finding fame following The Parent Trap a little tough to deal with. But Freaky Friday drew her in, as she related to IGN, because of the script. “It was just, like, ‘Wow, this would be perfect for me to come back with.’ I saw the original Freaky Friday, but this is very different from the original. It’s the same structure: the mother-daughter switching places, but my character is punk rock, which is kind of tom-boyish, but it has more of an edge.”

‘Confessions of a Teenage Drama Queen’ (2004)

What It’s About: “Lola” Steppe absolutely believes that her home city revolves around her, and is in for a very rude awakening when her family moves to the suburbs. Nothing is the same.

Behind-the-Scenes: “I instantly related to Lola,” Lindsay once said. “And the thing that got me interested in this movie is that I felt others would relate to it, too. This movie really tells it like it is, about how girls are in school and what really goes on. The other thing is, Lola is just such a different character from the one I played in Freaky Friday. It’s good to see how she develops throughout the story. She brings out the fun and the good in people. She helps her friend, Ella, to become the person she truly is and changes herself at the same time. It’s fun to do different things and switch on and off and see what I’m capable of.”

‘Mean Girls’ (2004)

What It’s About: Cady Heron, who spent much of her youth in Africa where she was raised by her scientist parents, moves to America and starts to attend public school. There, she discovers social cliques, falls in love for the first time, and finds herself on a personal quest to take down Regina George, the leader of “The Plastics” and pretty much the cruel ruler of the student body. In the process, though, Cady teeters dangerously close to losing herself.

Behind-the-Scenes: Enthuses Lindsay, “I think [writer] Tina Fey did a great job of getting into girls’ heads. The script is very realistic, very true to high school and the rivalry that goes on there. All kids go through a lot of phases until they find themselves, and the environment in school doesn’t help. In Cady’s case, she gets caught between the Mathlete World, where being a good student is what it’s all about, and the Plastic World, where being liked is the most important thing. I think every girl going to high school now, who will go or who already went, can relate to this. I certainly did.”

Read our exclusive interview with Erika Henningsen, who plays Cady in the Broadway musical version of Mean Girls!

‘Herbie: Fully Loaded’ (2005)

What It’s About: Maggie Peyton, the new owner of Herbie the Love Bug, wants to enter Nascar with “him.”

Behind-the-Scenes: “I had seen the original movie, and I loved that it’s the kind of story that gets passed down from one generation to the next,” she says. “There’s something about Herbie that is so magical and special, you really care about him as a kind of person, and it’s hard to even think about him as just a car! I also thought it would be really cool to do a movie that appeals to kids as well as to all those adults who grew up with Herbie. And to get to learn to race cars on top of all that was just too awesome to resist.”

“Maggie’s a great character — a tomboy with a kind of surfer vibe, who has fulfilled her need for speed doing all kinds of tricks on her skateboard,” she adds. “Still, she has this feeling that she has the talent to be a great racer, even if her dad is too worried about her to let her go out on the track. Somewhere inside her she just knows she has to go after her dreams — and Herbie takes her there. He even learns a thing or two about skateboarding!”

‘A Prairie Home Companion’ (2006)

What It’s About: A final gathering of country western stars at a celebrated radio show about to end its long run takes place, and the audience witnesses what goes on behind stage. Lindsay plays Lola Johnson.

Behind-the-Scenes: “I wasn’t aware of exactly what it was,” Lindsay admits to Cinemablend. “I spoke to my grandmother about it and she kind of informed me what it was about. The movie was coming together, and then I heard Meryl Streep’s name, then I heard Michelle Pfeiffer at one point, and then it finally just came together one day. They said, ‘Okay, we’re making the movie, and they want you to be Meryl Streep’s daughter in it.’ My role kind of got bigger as we went along, because I became friends with Garrison Keillor. It was amazing, and I would look at the call sheet and I would just see these actors that I didn’t believe were coming onto the set every day. It was a wonderful experience and good experience for me as my first independent film. It was nice to be able to sing live, and it’s just one of those movies where it’s always nice to have to look back on. It’s an amazing, monumental film and cast in it’s own way.”

‘Just My Luck’ (2006)

What It’s About: Ashley Albright, who everyone considers the luckiest woman in the world, suddenly finds her luck switched with that of a perennial loser (Chris Pine), and everything starts going wrong for her.

Behind-the-Scenes: “It’s a great story about coming of age and I thought it would be the perfect part for me to transition into adult roles,” says Lindsay. “Ashley has got her head on straight and she’s determined, which I think is great. But she has never been tested; she has never known what it’s like to really work for something and through that experience learn what life is.” The physical comedy, she adds, was a bit tough. “You don’t realize how hard it can be until you’re actually there. You’re reading the script and you say, ‘Oh, that’ll be so much fun to do,’ but then you perform the action or stunt, and that’s the hard part. But it’s fun when you can just let go and free yourself.”

‘Bobby’ (2006)

What It’s About: The assassination of Senator Robert F. Kennedy told through the lives of 22 people at Los Angeles’ Ambassador Hotel, where he was killed. Lindsay’s character’s name is Diane Howser.

‘Chapter 27’ (2007)

What It’s About: The story of Mark David Chapman (Jared Leto) in the days leading up to his assassination of John Lennon. Lindsay is Jude Hanson, a woman who encounters him.

Behind-the-Scenes: “During filming, there was an intense energy that comes over you,” offers Lindsay in an official interview for the film, “and somewhat of a sadness, because you know what went on there. I was a big fan of the character and I loved how she appreciated the music and what it was, because I think without music in the world I don’t know how I’d get through filming or just go through the day.

“I love John Lennon,” she adds. “I’ve always been a huge Lennon fan and Sean and Yoko. I look up to them so much. With Jared, I didn’t really speak to him much on the film, because he was kind of in his own world and really got into Mark Chapman’s mindset, so it kind of freaked me out a little bit. But I think the character of Jude sees Mark as a vulnerable fan; similar to her.”

‘Georgia Rule’ (2007)

What It’s About: A young woman (Lindsay’s Rachel) goes to her grandmother’s for the summer, attempting to hide a secret that could destroy her family. Jane Fonda and Felicity Huffman star.

Behind-the-Scenes: Lindsay was the first star signed for the film. Says the actress, “The script reminded me of Ann-Margret’s character in one of my favorite films, Kitten With a Whip. She was very Lolita-esque as well. Rachel doesn’t understand the difference between love and sex in a lot of ways. I think it’s important to play the character so any girl or boy that has ever gone through a situation like this can hopefully learn from.” The presence of Jane Fonda caused Lindsay to get a bit starstruck: “I dressed as her in Barbarella for Halloween one year… it’s a very small world. I just feel very lucky to work with people I’ve always admired.”

‘I Know Who Killed Me’ (2007)

What It’s About: Aubrey Fleming is someone who shows up after missing for a long time, but claiming to be somebody entirely different.

Behind-the-Scenes: The edgy nature of the script was the thing that drew Lindsay in, even before she’d finished reading it: “I e-mailed them after I had read just a few scenes and said, ‘I’ll do it.’ One of the scenes I read was the stripping scene. Initially, I thought, can’t they rewrite some of that? But in the end, it was part of what really interested me. The second I said I couldn’t do certain things, I thought, ‘Okay, I have to do it.’ For me to be able to be doing the things that I’ve done in this movie, I needed a director I was on the same wavelength with. I also had my first love scene. I wouldn’t even call it a love scene, it’s a sex scene.”

Although Lindsay has been dancing most of her life, her character’s pole dancing scenes presented a new physical challenge. “It’s really hard getting on those poles,” she laughs. “It’s all upper body strength. There were these women that were upside down, sliding down headfirst, and then flipping over, and then going back up. I thought, ‘I can’t really do that.’ But the lessons paid off. I couldn’t believe I was dancing the way I was. I watched the footage, and I was just, like, ‘Oh my God.’”

‘Machete’ (2010)

What It’s About: After being set-up and betrayed by the man who hired him to assassinate a Texas Senator, a man launches a brutal rampage of revenge against his former boss. Lindsay plays April Booth, described as “a socialite with a penchant for guns” as well as “a nun with a gun.”

Behind-the-Scenes: Explains Lindsay, “April was born into a life of privilege and takes everything she has for granted. But she undergoes a big change. As an actress, I like pushing the envelope.”

‘Inappropriate Comedy’ (2013)

What It’s About: Here’s how the movie is officially described: “In this comedy film, a computer tablet full of the world’s most hilariously offensive apps breaks through the borders of political correctness, stirring up cultural anarchy.”

Behind-the-Scenes: Lindsay’s role is just a cameo, though there’s no doubt that she took great delight playing a Marilyn Monroe-like starlet who decides to pull out a pair of guns to blow away the paparazzi that she feels is stalking her.

‘The Canyons’ (2013)

What It’s About: Tara (Lindsay) has an affair with her co-star on a film project, triggering her boyfriend to strike back in a violent and bloody manner.

‘Among the Shadows’ (2019)

What It’s About: A private investigator (Lindsay) must unravel the murder of her uncle while keeping secret the fact that she is a descendant from a line of werewolves.