Finding yourself just feet away from Lindsay Lohan on the red carpet is a surreal experience as a millennial woman. Growing up she was that girl. The star of every film you watched at sleepovers, the teen idol on the pages of every magazine. I once dyed my hair red to try to look like her.
Then, she became a cautionary tale of going off the rails and tanking a promising career – or an example of the cruelty of the paparazzi-fuelled media circus of the era that tortured high profile young women into breakdowns.
Lohan, now 39, still radiates that star quality. Whether it’s the pickled beetroot she credits for her incredible skin, or the deep plane facelift that half of Hollywood seems to be opting for: it’s working.
But it was never her bone structure that was her biggest asset. Lohan was always a genius comedic actor. I’m bound to secrecy on the finer details of Freakier Friday but, if Disney will let me, I’d say she’s never been better.
After various attempts at a comeback with highly variable results, it’s a joy to see her back and on top of her game. Before Freakier Friday hits cinemas on August 8, let’s talk a journey through her career timeline:
The Nineties break-out
After stints as a child model, Lohan’s big break comes with Disney’s The Parent Trap, a beloved tale of separated twins who reunite at summer camp and switch places to cause high jinks.
Actors playing duel roles is having a moment currently, with Michael B. Jordan and Robert Patterson winning plaudits for pulling a double shift in Sinners and Mickey 17 respectively. These are adult men – Lohan did it all at just 12 years old.
The golden years
The actor cemented her teen idol status with a run of lead roles in hit films. In Freaky Friday (2003) she played a grungy rocker teen body swapping with Jamie Lee Curtis as her mother. Those big chunky highlights became the look for teen girls to attempt to recreate with box dye and a dream. Next she landed the lead role in Confessions of a Teenage Drama Queen (2004) after Hilary Duff backed out, starring opposite Megan Fox in her screen debut.
And then there was Lohan’s magnum opus – Mean Girls (2004), where she played wannabe popular girl Cady Heron. The film made $67 million at the box office and became an instant cult classic. Lohan was the darling of Hollywood before her 18th birthday. But where co-stars Rachel McAdams and Amanda Seyfried would go on to have stellar careers, the wheels started to come off for Lohan.
Cat fights and pop albums
In 2004, Lohan was 17 and living on Sunset Boulevard, driving a BMW X5 and enjoying some light underage clubbing. This was when the press christened her LiLo, and breathlessly reported her every move.
She was feuding with Duff, after both stars dated singer Aaron Carter. Duff gatecrashed the Freaky Friday premiere, so Lohan snuck onto the red carpet of Cheaper By The Dozen. She allegedly called up Chad Michael Murray, her Freaky Friday co-star, to spread rumours about Duff while the were filming A Cinderella Story.
Lohan also flirted with a pop career. Her debut single ultimate was on the Freaky Friday soundtrack, then she released Speak (2004) and A Little More Personal (Raw) (2005) in quick succession. People forget this period of Lohan lore, but her song Rumours was an absolute banger.
Partying with Paris
The year is 2006 and the photograph of the decade is taken when Lohan is photographed in the front seat of a car with Britney Spears and Paris Hilton outside the Beverly Hills Hotel – forming an It Girl trinity.
Hilton has since cast this moment in a different light. In an interview with Andy Cohen, the heiress DJ claimed that Lohan “totally party-crashed” by jumping in the car with her and Spears. It was the beginning of a simmering feud that still occasionally bubbles over, with Hilton branding Lohan “pathetic” in a 2019 interview.
Lohan continued her acting career, but her behaviour on set while filming Georgia Rule with Jane Fonda in 2006 raised some eyebrows. A memo from James G. Robinson CEO of the production company was leaked to The Smoking Gun, where Lohan was described as "discourteous, irresponsible and unprofessional” for turning up to set late and Robinson threatens to sue her over production delays. Georgia Rule flopped at the box office.
Lohan versus the law
In 2007, things started to go rapidly go downhill for Lohan, who went on to be arrested a reported six times. She entered rehab for the first time at the Wonderland Center while filming I Know Who Killed Me (2007) and attended AA meetings.
Her first arrest happened in May that year after she wrecked her Mercedes in Beverly Hills and was charged with driving under the influence and possession for cocaine. This time she checked into rehab at the Promises Treatment Center. Then in July she was charged with the same, plus driving with a suspended licence, after chasing a woman in her SUV.
Lohan pled guilty and was sentenced to a day in jail, 10 days community service, and three years of probation. She checked into the Cirque Lodge Treatment Center for three more months of rehab. She then served 84 minutes of jail time before being released due to overcrowding.
Thus began a whole saga, with her probation extended in 2009 after she failed to attend a court-ordered substance abuse programme. Probation was revoked in 2010 when she skipped a court date to go to Cannes Film Festival.
She was fitted with an ankle monitor, but ended up in jail (again) after missing those court-ordered classes (again) and spent two weekslocked. Lohan spent 23 days in court-ordered inpatient rehab, then checked into the Betty Ford Center, a celebrity favourite. Not before being interviewed by Piers Morgan for the Daily Mail, where she said "constantly sending me to rehab is pointless” and denied her relationship with ex-girlfriend Samantha Ronson means she’s queer.
During her stay, an employee at the centre alleged Lohan attacked her during a routine substance test. They reached a civil settlement. Lohan was back in court at the start of 2011, accused of stealing a $2,500 necklace within days of leaving rehab.
Comeback attempt 1.0
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At 26, Lohan made her first attempt at staging a comeback in her acting career with Liz & Dick, a 2012 television biopic of Elizabeth Taylor and Richard Burton. The producers took out "incarceration insurance” as Lohan was still on probation.
In an inauspicious start, Lohan crashed a borrowed Porsche into the back of an 18-wheeler and is hospitalised then arrested. The show was savaged in the press, with the Hollywood Reporter’s critic snarking that Lohan is “more memorable in the tabloids than she was as an actress”. Ouch.
In 2013 Lohan was cast in The Canyons, a low-budget erotic thriller written by Bret Easton Ellis where she starred opposite porn star James Deen. The film also flopped. Although Lohan’s performance was praised, she declined to promote the film to protect her sobriety. During this period she also worked with Oprah Winfrey on a docuseries covering her journey through rehabilitation.
Lohan headed to London’s West End in 2014 to star in Speed The Plow at the Playhouse Theatre. The Standard’s theatre critic describes her performance as “competent — without being exciting” but only rated the production as two stars. Lohan completed her probation the next year.
Beach club boss business lady
Lohan officially moved to Dubai in 2014, where she has been based ever since, and began reinventing herself as a businesswoman. She dated Egor Tarabasov, a Russian real-estate mogul based in London, but the pair split acrimoniously in 2016 after an altercation at her house in Knightsbridge where police were called. Lohan later went on Russian TV and accused Tarabasov of attempted strangulation.
That same year, Lohan opened a venue in Athens called Lohan Nightclub. Lohan Beach House Mykonos and Lohan Beach House Rhodes followed in 2018. The Mykonos club served as a backdrop to a 2018 reality TV series from MTV called Lindsay Lohan’s Beach House.
2018 also saw Lohan in headlines again after a bizarre Instagram Live she posted where she approached a family of Syrian refugees sleeping rough in Moscow. Lohan appears to have offered to take two children back to her hotel, before things escalate and she demands to take them and their mother pushes her away. Lohan later told Paper Magazine: "I read the situation wrong. I've learned from it.”
Lohan sold the beach clubs in 2019 and signed up to be a panellist on Australia’s Masked Singer. She was unable to return for the second season due to coronavirus pandemic travel restrictions between London and Melbourne in 2020.
The second comeback
In 2021, Netflix announced that Lohan would make her acting comeback with a Christmas film called Falling For Christmas. Released for the holiday season in 2022, it featured Lohan as a spoilt heiress who loses her memory in a skiing accident and ends up working at a struggling mountain B&B run by a hot widower.
It was predictably schmaltzy fare, but it was Netflix’s most-watched holiday film in the US that year. Lohan shone and signed a two-movie deal with the streamer for two more seasonal rom-coms: Irish Wish (2024) and Our Little Secret (2024).
Irish Wish went down like a pint of cold sick with the critics – Vulture called it “a Crypto-Fascist, AI-Generated Harbinger of Doom” – but Lohan was credited with carrying the movie. Our Little Secret did better, but critics bemoaned that Lohan’s talents were wasted on the holiday movie industrial complex.
Lohan also found happiness in her personal life during this period. In 2022 she married Kuwaiti financier Bader Shammas, and they welcomed a son named Luai in 2023. The couple are relatively private, but Lohan does occasionally share snaps of family life on Instagram.
The comeback, for real this time
Finally, Lohan is back making movies with Disney. The sequel to Freaky Friday was announced back in 2023, and Freakier Friday premiered in London last week. The film sees Lohan re-unite with Curtis and Murray and it’s a true comeback for Lohan.
Looks like LiLo’s career managed to outlive the days of the tabloid salad days that gawked at her mistakes.
