Lindsay Lohan's Head-Turning Transformation

Lindsay Lohan's life has been more "Confessions of a Teenage Drama Queen" than "Our Little Secret." Lohan gained serious success as a child actor with an incredibly promising career, but, sadly, her very public addiction issues and arrests cast a shadow over her once bright star. 

The many controversies could have been a career-ender for someone less determined, but Lohan stayed resolute and focused on her health, carving out a more stable life for herself away from Los Angeles. She eventually made a triumphant return to our screens as an in-demand actor, wife, and mom with an inspiring comeback story worthy of its own movie — or juicy celebrity memoir. 

"I feel a huge sense of gratitude just to have lived through so many different experiences in life. I really have seen it all," Lohan told Flaunt in 2024. But despite some tough times, the "Irish Wish" actor isn't looking back with negativity. "I live without regrets. I think everything that has happened, I've learned from, and I'm grateful for that," she said. The star's no doubt made it through a lot of highs and lows, which have made her transformation totally head-turning.

Lindsay Lohan was born in 1986 and it wasn't long before stardom began calling her name. Lohan was just 3 years old when her parents Dina and Michael Lohan launched her modeling career, which quickly transformed into commercial appearances. "My mom was in the business. She was a Rockette, and my dad was also in the business. So that's basically how I got into acting," a 12-year-old Lohan told the Golden Globes in 1998.

But the promising star's life behind the camera was less rosy. The actor grew up fast and took on a parental role to take care of her younger siblings Ali Lohan, Michael Lohan Jr., and Dakota Lohan, amid their parents' marital strife. "I feel like a second parent in the sense that I helped raise my family," she told Allure (via Today) in 2006. "I was put between my mother and father a lot. Well, I would put myself between them to try and keep the peace, and I felt good doing that." 

The star also revealed that being on set so young influenced not only her career, but her personality. "[As a child actor] they teach you to say 'yes' to everything, and that's not really what life's all about," she told Bustle in 2024.

It didn't take long for Lindsay Lohan to gain mainstream success. At age 12, the young actress landed a role in the 1998 Disney movie "The Parent Trap," which ended up being her big break. "I auditioned in New York City, and I had about three callbacks. Then I flew out to Los Angeles and screen-tested," she told the Golden Globes in 1998. Once Lohan got the part, she only had about a week to pack before flying to London to film. 

The movie was a big success, making over $92 million globally, and Lohan credited it with introducing her to a love of acting. "Without this movie, I wouldn't have gotten the acting bug. How do you not want to act for the rest of your life after doing a film like this?" she said during a 2020 virtual reunion. "The Parent Trap" got Lohan's foot in the door for other blockbusters too, and she continued to appear on red carpets in some very Hallie Parker and Anna James-esque outfits. In 2000, she appeared in "Life Size" with Tyra Banks, and in 2002, she starred in the Disney Channel's "Get A Clue." 

But while Lohan's career was taking off, her family life was falling apart. "My parents were kind of separating at the time [of 'The Parent Trap']. And it made it a lot easier for me to play these characters that were figuring it out," Lohan said. Dina and Michael Lohan divorced in 2005, a major milestone in Lohan's complex relationship with her father. 

By 2004, Lindsay Lohan was a true multi-hyphenate. She'd become a household name thanks to her role as Cady Heron in the hugely successful teen movie "Mean Girls," rocking a red carpet look we'll never forget at the premiere, and was ready to become a popstar.

The New York native had already dipped her toe into the music world by releasing "Ultimate," for the "Freaky Friday" soundtrack, and "Drama Queen (That Girl)," for "Confessions of a Teenage Drama Queen." But she explained her solo music would be different during a 2004 IGN interview. "[Those songs] weren't Lindsay at all, so those had nothing to do with me and my musical career," she said, explaining she performed the tracks as the characters she portrayed in the movies. 

"Singing a song that's on my album, I have more feelings towards it, because more of how I feel is put into it and it's ... personal things that I've learned and experienced," Lohan said. She dropped her first official single, "Rumors," that September. Her first album, "Speak," followed three months later, and both were successes for the teen idol. "Speak" was certified platinum, selling over 1 million copies, while "Rumors" was certified gold.

Lindsay Lohan was one of the biggest stars in the world by 2005, but the cracks were starting to show. She told the Los Angeles Times she was surviving on around three hours of sleep a night because of her busy schedule and mounting pressure. "I can never sleep because I'm always thinking about what I can be working on next, going over ideas, writing stuff down. I push myself, and I don't want to disappoint people," she said. 

The teenager was also spotted at nightclubs. "I was going out every night because my friends were, and I thought if I wasn't going out then I was going to miss out on something," she said, adding that the team on her movie "Herbie Fully Loaded" had spoken to her about ensuring she stayed professional. Things worsened the following year when she was hospitalized on the set of the movie "Georgia Rule." Lohan's rep told The Insider (via People) she was okay but had been treated for dehydration. Still, rumors swirled partying may have contributed to her health scare.

The producer of "Georgia Rule," James G. Robinson, scolded Lohan for skipping a filming day with no warning, which cost the production company $500,000. "I wrote a letter to her ... I basically said 'Let's knock it off, get to work. I'm not going to put up with it.' And she was fine, she came to work every day after that," he told CBS News in 2007.

Though Lindsay Lohan was still in demand in 2007, releasing movies including "I Know Who Killed Me," her career suffered multiple setbacks. That January, she was hospitalized with appendicitis and entered rehab shortly after. As she focused on her wellbeing, she was forced to pull out of big commitments, including a role in the movie "A Woman Of No Importance." She doesn't want to just (say) yes (to) everyone and compromise herself anymore," her publicist told Hello. "What she needs comes first — and right now she needs focus."

But things went from bad to worse following her rehab stint. That May, Lohan was arrested for driving under the influence, and in July, she was arrested again for a DUI and possession of cocaine. In August, the "Mean Girls" star pleaded guilty to various charges and was ordered to spend one day behind bars (although she only spent 84 minutes in jail). 

"My life has become completely unmanageable because I am addicted to alcohol and drugs," she said in a statement, according to People. "Recently, I relapsed and did things for which I am ashamed. I broke the law, and today I took responsibility." Still, Lohan struggled with the party girl label she'd been given. "I lived maybe six months out of my life like that, doing something wrong, and then I stopped," she told Interview in 2009.

Though Lindsay Lohan's life was a little quieter following her brief prison stint, her legal issues returned in 2010. In May, Lohan appeared at the Cannes Film Festival and missed a probation hearing, so a warrant was issued for her arrest. Two months later, Lohan was visibly upset in court when a judge ruled she'd violated her probation. She was sentenced to 90 days in prison and ordered to complete a substance abuse program. 

The "Freaky Friday" star was released from prison in August after about two weeks, allegedly due to overcrowding. The following month, she failed a drug test and returned to jail before checking into rehab once again. Lohan's career was on the backburner amid her very public issues, and her tough time saw her lose gigs. The actor had landed a role in the movie "The Other Side," but writer and director David Michaels told TMZ he'd decided not to cast her. 

Lohan remained undeterred. "I want my career back. I want the respect that I had when I was doing great movies. And if that takes not going out to a club at night, then so be it. It's not fun anyway," Lohan told Vanity Fair. But she still couldn't stay out of prison. In 2011, Lohan was sentenced to a further 120 days in jail and 480 hours of community service for violating her probation again.

Lindsay Lohan's career was looking up in 2013. She earned a handful of acting credits, including a guest role in "Anger Management" and roles in the movies "The Canyons" and "Scary Movie 5." Lohan also entered rehab again and opened up to the world about her addiction and struggles.

That May, she told Daily Mail she'd been court-ordered to rehab six times. "My two DUIs were totally irresponsible — a stupid mistake," she said. "Everyone thinks I'm this crazy drug addict who shows up late to everything and behaves so badly. But I'm not." Three months later, Lohan sat down with Oprah Winfrey on "Oprah's Next Chapter" and spoke candidly about her journey to sobriety and her determination to stay clean. "I have such a desire to want to keep this feeling and stay this way, and I'm willing to do whatever it takes," she said (via People).

The star's life took a positive turn when she swapped Hollywood for London in 2014, landing a gig in a West End play. "In LA I didn't know what to do apart from go out every night," she told The Guardian. "I needed to grow up and London is a better place for me to do that than anywhere else," she added, vowing never to live in Los Angeles again. And she meant it. Later that year, she said toodle-oo to London and started a new life in Dubai.

After moving to Dubai, Lindsay Lohan's life became much more stable. The former child actor shunned the spotlight for a few years, but returned to TV in 2019 to produce "Lindsay Lohan's Beach Club." The MTV series followed her as she ran a club in Greece, but didn't return for a second season after she sold the property for a major payday. The talented star made a handful of other appearances on the small screen too, including as a judge on "The Masked Singer" in Australia.

She was also determined to return to music — a source told Us Weekly she'd signed a new record deal in 2019. "Lindsay is really excited to be working on new music. It's been a minute since she's been in the studio, but she got right back into the recording process and has been putting in a lot of time." That September, the star dropped the track "Xanax" and followed it up with "Back To Me" in 2020.

But her music career wasn't her only focus. Lohan revealed on CNN's "New Year's Eve Live" in 2019 that she had big plans to move back to the U.S. "[I want to] come back to America and start filming again, which, I'm doing something soon, in this New Year. And, you know, just taking back the life I've worked so hard for," she said.

Things were very much looking up for Lindsay Lohan in 2021. In May, she began her mainstream acting comeback when she signed a deal with Netflix to star in and executive produce the Christmas rom-com "Falling For Christmas." "I was excited to kind of come back, to do something with Netflix, who is a big family in a way. It was the right fit for me, especially to be able to executive produce it," Lohan told Cosmopolitan in 2022. 

"Falling For Christmas" was a huge hit, and Lohan celebrated its success on Instagram. "I can't even begin to tell everyone how grateful I am for this incredible moment! To all of the fans and longtime believers in me, I appreciate you. My heart is filled with so much love and gratitude," she wrote. 

The star's personal life was at an all-time high, too. In November, the "Bossy" singer confirmed her engagement to Bader Shammas. "My love. My life. My family. My future," she captioned adorable Instagram photos of them together, showing off her engagement ring. In July 2022, Lohan confirmed their marriage in a Facebook post, referring to Shammas as her husband. "I am stunned that this is my husband. My life and my everything. (E)very woman should feel like this everyday," she gushed in the caption.

Life got even better for Lindsay Lohan in 2023. The pregnant star showed off her baby bump in a June Allure photoshoot and confirmed she still lived in Dubai, despite teasing a return to the States. "Dubai gives me that space to have my own vision of what I need to do next," she said. The following month, she and Bader Shammas welcomed their son, Luai. Lohan appeared to be on better terms with her parents, too. Her dad shared a since-deleted family photo on Instagram that showed them enjoying dinner in New York before she and Shammas returned to Dubai. 

The "Mean Girls" star has made no secret of the fact she's happier than ever. "[My struggles] made me so much stronger. I feel I've empowered myself in a lot of ways and that feels great," she told Flaunt in 2024. After years of Lohan changing up her hair, she also finally felt comfortable rocking her natural red tresses (which was actually 2023's hottest hue). "It did take some time to fully embrace it as one of my trademarks," she told Byrdie. "I always found myself coming back to my natural red. There's something special about it — it feels uniquely me."

While we wouldn't blame her for retiring to a quiet life in the sun with her husband and son, Lohan won't be resting on her laurels. She shared her future plans with Flaunt, revealing, "Starting my own business and producing more things that I love are part of where I want my future to take me."

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).