Lindsay Lohan, 39, Looks Effortlessly Stunning Nearly Three Decades After ‘The Parent Trap’ Made Her a Star

Lindsay Lohan began her career as a child model with Ford Models at just three years old, appearing in campaigns for Calvin Klein Kids and Abercrombie, as well as in over 60 television commercials for brands like Pizza Hut and Wendy’s, including a Jell-O spot with Bill Cosby.

By age ten, she had already acted in the soap opera Another World as Alexandra “Alli” Fowler, and was described by Soap Opera Magazine as a “show-business veteran.” She stayed on the show for a year before landing her breakthrough role in Disney’s 1998 family comedy The Parent Trap, where she played twins attempting to reunite their divorced parents.

The film earned $92 million worldwide, and critics praised Lohan’s ability to create two distinct personalities. Her performance won a Young Artist Award and secured her a three-film contract with Disney, firmly establishing her as a rising star.

In 2003, Lohan starred in Freaky Friday alongside Jamie Lee Curtis, playing a mother-daughter duo who switch bodies. Her character was rewritten at her own suggestion, and critics, including Roger Ebert, lauded her performance, comparing her focus and seriousness to that of Jodie Foster. The film earned $160 million worldwide and won her the MTV Movie Award for Breakthrough Performance. She also contributed to the soundtrack, singing the song “Ultimate” for promotion.

In 2004, she appeared in Confessions of a Teenage Drama Queen and, more significantly, Mean Girls, a teen comedy written by Tina Fey. Mean Girls grossed $129 million worldwide, received critical acclaim, and cemented Lohan’s status as a teen icon. She won multiple Teen Choice Awards and MTV Movie Awards, and her fame skyrocketed, with tabloids documenting her personal life and partying habits.

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In 2004, at age 17, Lohan released her debut album, Speak, which sold over a million copies in the United States. Its singles, including “Rumors” and “Over,” performed well, though critics gave the album mixed reviews. She continued her Disney run in 2005 with Herbie: Fully Loaded, which earned $144 million globally. Lohan released a second album, A Little More Personal (Raw), later that year, which she co-wrote and directed the music video for its lead single.

However, her career soon faced turbulence. Films like Just My Luck (2006) were poorly received, and Lohan’s off-screen struggles began impacting her work. She took on smaller, independent roles, including A Prairie Home Companion (2006) and Bobby (2006), earning praise for her performances but struggling with personal challenges. I Know Who Killed Me (2007) marked a low point, earning critical backlash and Golden Raspberry awards, while her public image was further complicated by arrests and rehabilitation stints. She withdrew from several projects, including A Woman of No Importance and The Edge of Love, due to personal difficulties, highlighting her instability at the time.

Between 2008 and 2013, Lohan’s work was a mix of independent films and television appearances. She starred in Labor Pains (2009), guest-starred on Ugly Betty, and appeared in Machete (2010). She also narrated the BBC documentary Lindsay Lohan’s Indian Journey (2010) and faced production and distribution challenges with films like The Canyons (2013). She hosted Chelsea Lately and appeared in Scary Movie 5, but critical reception was inconsistent.

In 2014, Lohan’s docu-series Lindsay aired on OWN, showing her move to New York City post-rehab. She also made her stage debut in London in Speed-the-Plow, earning mixed reviews.

Lohan gradually returned to mainstream attention through fashion, entrepreneurship, and reality TV. She launched a clothing line, 6126, and worked with brands like Jill Stuart, Fornarina, and Allbirds. She opened beach resorts in Mykonos and Rhodes and released jewelry and nursery accessory lines. Lohan also ventured into digital media with her game app Lindsay Lohan’s The Price of Fame (2014) and her lifestyle site Preemium (2017). In 2022, she hosted the podcast The Lohdown.

Her return to acting was marked by Netflix projects. In 2022, she starred in Falling for Christmas, her first major role in over a decade, performing songs for its soundtrack. The film was the most-watched holiday release in the U.S. that year.

She then starred in Irish Wish (2024) and Our Little Secret (2024), receiving praise for her performances. In 2025, she reunited with Jamie Lee Curtis for Freakier Friday, earning global box office success. She is also set to star in and produce Hulu’s series Count My Lies, marking her first starring TV role.

Lohan’s career is defined by early success, turbulent personal challenges, and a determined resurgence. From child model to Disney darling, teen star, tabloid figure, and now a multifaceted artist and entrepreneur, she has continuously reinvented herself. Her talent, combined with her resilience, has allowed her to navigate a difficult industry while exploring music, fashion, hospitality, and streaming projects, proving that she remains a captivating figure in Hollywood nearly three decades after The Parent Trap launched her career.

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