Lindsay Lohan Through the Years

Lindsay Lohan is no stranger to the spotlight.

After modeling as a child, Lohan starred as twins Annie James and Hallie Parker in 1998’s The Parent Trap alongside Dennis Quaid and Natasha Richardson. Following the movie’s success, she scored a three-film contract with Disney.

“I was 10 when I did Parent Trap,” Lohan recalled to Rolling Stone in 2004. “I left school for eight months. When I came back, my friends were like, ‘Where’d you go?’ I said, ‘My family and I went on a long vacation.’ Then the movie came out, and they were like, ‘Um, Lindsay? That’s you in Parent Trap.’ And I said, ‘Oh, yeah. I also did this movie while we were gone.’”

While Lohan’s success in Hollywood continued with the release of Mean Girls in 2004, her personal issues began to overshadow her career and she appeared in court more than 20 times amid her substance abuse struggles from 2007 to 2012.

While reflecting on some of her darkest hours, Lohan revealed at the time that she had no regrets about her troubled past. “I believe things happen for a reason,” she said in 2013. ”I live without regrets. There are certain things I have done, mistakes that I made, that I would change, but I don’t regret them at all, because I’ve learned from them.”

After taking a break from acting, Lohan shifted her focus to opening nightclubs overseas before returning to the screen in Netflix films like Falling for Christmas, Irish Wish and Our Little Secret.  She also made cameo in the 2024 Mean Girls movie musical adaptation and filmed her Freaky Friday sequel, Freakier Friday, which is due out in 2025.

Scroll through to see photos of Lohan through the years: