Photos of Lindsay Lohan Then vs. Now

A Child Star

A Child Star

Lindsay Lohan was born to shine! Growing up in New York, she started modeling at just three years old. With her fiery red hair and adorable smile, she quickly became a favorite in commercials for brands like Jell-O and Pizza Hut.

Lindsay’s big break came in 1998 when she starred in The Parent Trap. Playing twins Hallie and Annie, she wowed audiences with her charm and talent. Who could forget her British accent and those hilarious pranks?

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The Teen Years

The Teen Years

As a teenager, Lindsay Lohan was unstoppable. After The Parent Trap, she became a Disney darling, starring in Life-Size (2000) and Get a Clue (2002). These roles showcased her ability to balance humor and heart, making her a favorite among young audiences.

By her mid-teens, Lindsay was already a seasoned actress. She juggled acting with her budding music career, signing a record deal in 2002. Her teenage years were a whirlwind of auditions, red carpets, and growing fame, setting the stage for her iconic roles to come.

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"Freaky Friday"

"Freaky Friday"

In 2003, Lindsay Lohan starred in Disney’s Freaky Friday alongside Jamie Lee Curtis. Playing a rebellious teen who swaps bodies with her mom, Lindsay’s comedic timing and relatability shone. The film was a massive hit, earning over $160 million worldwide.

Freaky Friday catapulted Lindsay into teen stardom. Her performance earned her critical praise and an MTV Movie Award for Breakthrough Performance. This role solidified her as a leading actress and opened doors to even bigger projects.

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Queen of Mean (Girls)

Queen of Mean (Girls)

In 2004, Lindsay Lohan took on the role of Cady Heron in Mean Girls, a film that redefined teen comedies. Her ability to balance humor and vulnerability made Cady’s journey from outsider to queen bee unforgettable. The movie’s sharp wit and Lindsay’s charm struck a chord with audiences.

Lindsay’s performance in Mean Girls earned her a Teen Choice Award, marking her as a voice for her generation. The film’s cultural impact was massive, with Lindsay becoming a style and attitude inspiration for teens everywhere.

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A Pop Star Emerges

A Pop Star Emerges

Also in 2004, Lindsay Lohan expanded her talents beyond acting with the release of her debut album, Speak. Featuring pop-rock hits like "Rumors," the album showcased her vocal abilities and gave fans a glimpse into her personal life through music.

Speak was a commercial hit, going platinum and solidifying Lindsay as a multi-talented star. Her music resonated with teens, blending catchy beats with relatable lyrics. The album’s success proved she was a pop culture powerhouse.

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Struggles in the Spotlight

Struggles in the Spotlight

In 2007, Lindsay Lohan’s rising career took a hit as legal troubles began to overshadow her success. She faced multiple arrests for DUIs and possession of cocaine, leading to court appearances and a brief jail sentence. The media frenzy around her personal life was relentless.

Lindsay’s legal issues marked a challenging chapter in her life. Despite her talent, her struggles with substance abuse and probation violations became tabloid fodder. This period highlighted the pressures of fame and the difficulties of navigating adulthood under constant public scrutiny.

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A Turning Point

A Turning Point

In 2013, Lindsay Lohan’s legal troubles continued to make headlines. She faced charges for reckless driving and lying to police after a car accident in 2012. These incidents led to court-mandated rehab and community service, keeping her in the public eye for all the wrong reasons.

Despite the setbacks, 2013 marked a turning point for Lindsay. She completed a 90-day rehab program and began working on rebuilding her career. While her legal troubles were a struggle, they also highlighted her efforts to take accountability and move forward.

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"Lindsay Lohan’s Beach Club"

"Lindsay Lohan’s Beach Club"

In 2019, Lindsay Lohan made her reality TV debut with Lindsay Lohan’s Beach Club. The show followed her as she managed a luxury beach club in Mykonos, Greece. It offered fans a glimpse into her entrepreneurial side and her efforts to reinvent herself.

The series marked Lindsay’s return to the spotlight, showcasing her leadership and business acumen. While the show only lasted one season, it reminded audiences why they loved her and hinted at her determination to rebuild her brand in the entertainment world.

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A Christmas Miracle

A Christmas Miracle

In 2022, Lindsay Lohan made her highly anticipated return to acting with Netflix’s holiday romantic comedy Falling for Christmas. Playing a spoiled heiress who finds love and self-discovery after a skiing accident, Lindsay charmed audiences with her comedic timing and heartfelt performance.

Falling for Christmas was a new chapter in Lindsay’s career, reminding fans of her talent and on-screen charisma. The film’s success not only reignited her acting career but also introduced her to a new generation of viewers.

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A Star Reborn

A Star Reborn

Today, Lindsay Lohan is thriving both personally and professionally. After years of ups and downs, she’s embraced a quieter life in Dubai with her husband and son, while continuing to make her mark in entertainment. Her recent projects have reminded fans of her enduring talent and charm.

In 2025, Lindsay reunited with Jamie Lee Curtis for Freakier Friday, the highly anticipated sequel to their 2003 hit. Revisiting her role as Anna Coleman, Lindsay brought a fresh perspective to the character, now navigating life as a mother herself. The film’s success further cemented her comeback, proving that Lindsay’s star power is as strong as ever.

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