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:

Lohan won a Young Artist Award for her performance in the remake of the 1961 film.

Lohan continued to work with Disney in the early 2000s, starring alongside Tyra Banks in Life-Size, Brenda Song in Get a Clue and Jamie Lee Curtis in Freaky Friday.

Lohan’s teen queen status was solidified in 2004 following the releases of Mean Girls and Confessions of a Teenage Drama Queen. That same year, Lohan dropped her debut album, Speak.

As Lohan’s star continued to rise, she found herself making headlines for more than just her movies. In May 2007, she was arrested for a DUI and subsequently checked into rehab. Later that summer, she was taken into custody for possession of cocaine, driving under the influence and driving with a suspended license. After pleading guilty, Lohan was sentenced to one day in jail, ordered to complete an alcohol education program, community service and put on probation. She served 84 minutes in jail in November 2007.

The I Know You Killed Me star’s legal woes continued when she missed a mandatory hearing in 2010. A judge subsequently ruled that she violated the terms of her probation, sentencing her to 90 days in jail and 90 days of rehab. After 14 days in jail, Lohan was released early once again due to overcrowding.

Lohan tried to take back the narrative in the eight-part docuseries, Lindsay, in 2014.

The former child actress started developing a series of nightclubs in Greece in 2016. Three years later, she scored a reality show, Lindsay Lohan’s Beach Club, about her staff at the Mykonos, Greece, club. The show ran for one season on MTV in 2019.

Lohan, who turned 34 in July 2020, moved back to the United States from Dubai to manage her sister Ali’s music career and released her own music.

Lohan filmed a Christmas movie for Netflix opposite Glee alum Chord Overstreet, marking her first leading role since 2013. Falling for Christmas follows a spoiled heiress who gets amnesia while skiing right before Christmas and is taken in by a handsome lodge owner and his precocious daughter. The flick is due out in 2022.

The Confessions of a Teenage Drama Queen star announced her engagement to beau Bader Shammas in November 2021 after nearly two years of dating. “My love. My life. My family. My future. @bader.shammas #love 💍,” Lohan captioned an Instagram gallery from the proposal. The twosome were first linked in 2020 after being spotted together at a Dubai music festival.

Netflix announced a two-picture deal with the actress in February 2022. “We’re thrilled to continue our partnership with her,” Netflix’s head of independent productions, Christina Rogers, said in a statement. “We look forward to bringing more of her films to our members around the world.”

In November 2022, Lohan released a cover of “Jingle Bell Rock” as part of the soundtrack for her Netflix film Falling for Christmas. The rendition came out nearly two decades after the actress danced to the song in the teen classic Mean Girls.

Lohan announced in March she was pregnant and expecting her first child with her husband.

“We are very excited for our new family member to arrive and we are looking forward to this next chapter of our lives!” the I Know Who Killed Me star told Us in a statement at the time. She also uploaded a photo via Instagram of a baby onesie emblazoned with the words, “Coming soon.”

“We are blessed and excited!” she captioned the social media post.

Lohan showed off her bump in May, wearing a black one-piece while lounging poolside.

One month later, a source confirmed to Us that Lohan and Shammas are expecting a baby boy.

“She’s ready for motherhood. It’s always been a dream for her,” the insider shared. “She feels being a mom will make her a better actress, businesswoman and wife.”

Us confirmed in July that Lohan and Shammas welcomed “a beautiful, healthy son” named Luai.

After making a cameo in the Mean Girls movie musical adaptation in January, Lohan released two movies on Netflix: Irish Wish and Our Little Secret, which hit the streaming service in March and November, respectively. She also filmed her upcoming Freaky Friday sequel alongside Jamie Lee Curtis, which is set to hit theaters in 2025.