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‘I strangely somewhere inside knew and kind of wanted to go to jail’: Lindsay Lohan’s Hollywood comeback

At 38, the New York actress has become the latest major star to reach a new professional peak following a decade marked by scandals and setbacks. With just days to go before the release of her new Netflix comedy, we look back through images at her tumultuous fall from grace and her journey back to the limelight

Carlos Megía

Nov 17, 2024 - 05:15CET

After falling from grace, Lindsay Lohan is once again winning over major brands. High-profile labels like Balenciaga are inviting her to their fashion shows, reminding the public that if anyone embodies the Y2K style that’s currently back in vogue, it’s Lohan. She has recently been seen in the front row at the shows of esteemed brands like Saint Laurent, Michael Kors, and Balenciaga.WWD (WWD via Getty Images)

In July 1998, 'The Parent Trap' was released, marking Lindsay Lohan's film debut. And it was quite the debut: she had a starring role and played two characters, twins Annie and Hallie. The movie catapulted her to fame and made her one of Disney's most recognizable faces. Lohan went on to headline other notable Disney productions such as 'Freaky Friday' and 'Confessions of a Teenage Drama Queen,' but her performance in 'The Parent Trap' remains the most iconic of that era. This film, buoyed by 1990s nostalgia, has since become a beloved cult classic in the family comedy genre.©Walt Disney Co./courtesy Everet

Although she had been appearing in commercials since before she could read, Lindsay Lohan shot to global fame at the age of 12, making her debut on her first red carpet. With her signature red hair flowing freely and her distinctive freckles on full display, the young star wore a blue mini-dress adorned with white lace and wide straps. This marked the beginning of countless photocall moments to follow. Over time, her style would evolve dramatically, with fashion choices far bolder than that initial, endearing appearance in front of the cameras.Barry King (WireImage)

During her teenage years, the New York-born Lohan headlined youth cinema hits, most notably the iconic 'Mean Girls.' At that point in her career, her name guaranteed a movie would be a blockbuster. Released in 2004, 'Mean Girls' was about more than sharp humor: it offered a snapshot of the sexism, racism, and homophobia of its era, resonating deeply with an entire generation of young women. Many of its lines evolved into mantras for teenage girls amid the rise of MySpace and Messenger — and they continue to hold cultural weight in the age of Instagram and TikTok.CBS Photo Archive (CBS via Getty Images)

The image of Lindsay Lohan, Britney Spears, and Paris Hilton being swarmed by paparazzi as they exited a nightclub is one of the most defining snapshots of 2000s pop culture. Captured on a November night in 2006, it marked the last time the trio — dubbed the "Holy Trinity" —was photographed together. Soon after, all three would become tabloid staples for various problems: Paris Hilton faced jail time for drug-related charges, Britney Spears experienced a highly publicized breakdown and subsequent stint in rehab, and Lohan went through a combination of both. Paris Hilton recently revealed the backstory behind the photo: despite already being on bad terms with Lohan, the actress had jumped into the car to escape the relentless press. Bauer-Griffin (GC Images)

Lindsay Lohan's downward spiral began when she turned 20, slipping into a cycle of self-destructive behavior that, by her own admission, nearly claimed her life. The situation grew so dire that devoted fans shared photos online wearing T-shirts emblazoned with the plea, “Don't Die Lindsay.” Between 2007 and 2010, Lohan faced a series of highly publicized arrests for drunk driving, cocaine possession, jewelry theft, car accidents, and altercations, interspersed with frequent stints in various rehab centers. “Amid all the drama surrounding my life, people forget that I just want to enjoy my 20s and spend time with friends when I'm not working,” she told EL PAÍS. Industry sentiment, however, suggested otherwise. Nina Jacobs, the producer of 'Herbie: Fully Loaded', one of the films that solidified Lohan's status as a teen icon, remarked: “It is heartbreaking to see someone with such charisma and on-screen allure squander it.” Simultaneously, Lohan's fame took on a different edge, with men's magazines like 'Maxim' naming her the sexiest woman alive.Handout (Getty Images)

Branded as “Hollywood’s bad girl,” Lindsay Lohan was sentenced to 90 days in jail in 2010, but was only behind bars for 14. Her downward spiral continued, marked by repeated probation violations and subsequent sentences. This tumultuous period severely impacted her career; her unpredictable behavior on set, when she showed up at all, led directors to threaten legal action. Lohan’s reputation cost her coveted roles, including that of Linda Lovelace, star of the iconic erotic film 'Deep Throat,' even after promotional posters featuring her had already been released.DAVID MCNEW (POOL/AFP via Getty Images)

It's as quintessentially American as the Super Bowl halftime show, Thanksgiving turkey, or Halloween trick-or-treating: when a star seeks redemption after a public scandal, they sit down for a tell-all interview with Oprah Winfrey. Following in the footsteps of Michael Jackson, Lance Armstrong, and Meghan Markle, Lindsay Lohan candidly confessed her long-standing struggles with substance abuse to the legendary host in August 2013. “At that point ... I strangely somewhere inside knew and kind of wanted to go to jail,” she told the talk-show host. “I think it was just to find some peace and just have no choice but to just sit and be."SUPPLIED BY XPOSUREPHOTOS.COM (ND / Cordon Press)

Before meeting her current partner, the New Yorker had a tumultuous relationship with young Russian millionaire Egor Tarabasov, who physically and emotionally abused her on multiple occasions. Lohan called for help from her London apartment's terrace and during a vacation on the Greek island of Mykonos, where he assaulted her in front of other beachgoers. "I realise now you can't stay in a relationship just for love," she told 'The Daily Mail.' "No woman can be hit and stay with that person if that person isn't prepared to say sorry."David M. Benett

"I am the luckiest woman in the world," the actress said, reflecting on the profound impact meeting her current husband, Bader Shammas, has had on her life. The first whispers of their romance began in 2020, during a party in Dubai. Shammas, a discreet banker of Lebanese descent and an assistant vice president at Credit Suisse, kept a low profile. Two years later, the couple tied the knot.Amy Sussman (Getty Images)

There’s no stronger catalyst for a professional renaissance than nostalgia, and Lindsay Lohan knows that all too well. Earlier this year, as the musical remake of 'Mean Girls' premiered, 'Variety' revealed that Lohan had earned a cool half a million dollars for her brief cameo in the film. The appearance was kept under wraps until the premiere and completed in just half a day's work. In 2023, the original 'Mean Girls' cast, minus Rachel McAdams, reunited for a commercial for a department store chain ahead of Black Friday. It’s clear: the past always pays off.Jason Mendez (Getty Images for Paramount Pictu)

The actress became a mother for the first time at the age of 37 in July of last year, welcoming a baby boy named Luai, which means "strong" in Arabic. The little one was born in Dubai, where she and her husband have lived for several years. For Lohan, motherhood has been nothing short of a “blessing.” "I'm so grateful for every moment of it, just every second," Lohan told 'People' magazine. "Every morning waking up and running to grab my son and just looking at him and when he looks me back in the eyes, I'm going to get emotional." Jamie McCarthy (Getty Images for Michael Kors)

La prueba más fehaciente de que una intérprete vuelve a estar en la primera línea tras vivir años tumultuosos es que la gran multinacional por excelencia, y la más celosa respecto al comportamiento mediático de sus estrellas, Disney, quiera volver a contar contigo como uno de sus rostros visibles. Lohan lo ha conseguido con la secuela de Ponte en mi lugar (Freaky Friday), la comedia de enorme popularidad que protagonizó junto a Jamie Lee-Curtis en 2003 y en la que madre e hija intercambiaban sus cuerpos. La segunda parte llegará a los cines el próximo verano para demostrar que no hay nada que guste más en las colinas de Los Ángeles que una bonita historia de redención. Corey Nickols (Getty Images for IMDb)

The most undeniable sign that Lohan is back is the fact that she is once again being embraced by the biggest media powerhouse of them all — Disney. Lindsay Lohan has achieved just that, securing a role in the sequel to 'Freaky Friday,' the beloved 2003 comedy in which she starred alongside Jamie Lee Curtis, playing a mother and daughter who swap bodies. The highly anticipated sequel is set to hit theaters next summer, serving as a heartwarming testament to the power of redemption in Hollywood.Planet/ Cordon Press

A decade after her most tumultuous years, a revitalized Lindsay Lohan made an unexpected appearance as the international guest at Madrid Fashion Week. Drawn by the buzz surrounding Palomo Spain, Lohan attended various fashion shows in the city, donning creations by designers such as Jorge Vázquez, María Escoté, María Ke Fisherman, and Malne. She quickly became the center of attention, captivating audiences and making headlines. Lohan's Spanish escapade gained even more intrigue when she stopped by Casa Lucio to sample their famous 'huevos rotos' and made waves by following Spain's former prime minister Mariano Rajoy on Instagram.NurPhoto (NurPhoto via Getty Images)