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. The “Confessions of a Broken Heart (Daughter to Father)” songstress appeared in court more than 20 times amid her substance abuse struggles from 2007 to 2012.

“I got arrested for my first DUI when I was 20 and they found me with drugs,” Lohan told Piers Morgan in 2013. “And from then on the press were on me all the time. It was the first time I’d taken drugs; I was out in a club with people I shouldn’t have been with, and took cocaine, and got in the car. It was so stupid.”

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. In December 2019, the Herbie: Fully Loaded star announced she had plans for a Hollywood comeback.

“I’m managing my sister, so I want to really focus on me and everything that I can do in my life and come back to America and start filming again, which I’m doing something soon in this new year,” she told Andy Cohen and Anderson Cooper on CNN’s New Year’s Eve special. “And, you know, just taking back the life I’ve worked so hard for and sharing it with my family and you guys.”

Scroll through to see photos of Lohan through the years:

Sarah Hearon

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