Lindsay Dee Lohan first entered the Hollywood scene as a toddler. With her adorable, freckled face and natural charisma, Lindsay was a promising child star, born to be in the spotlight. She began in commercials before becoming a Disney Channel drama queen. The movie star is extremely gifted, but her wild antics and party-girl reputation overshadowed her talent.
Lindsay’s downward spiral began when she moved to LA and was getting caught stumbling out of bars all around Hollywood. She didn’t know how to handle her fame and fortune at such a young age. So, naturally, she followed the same dangerous path as many other child stars. From The Parent Trap to Lindsay Lohan’s Beach Club, here is the scoop on Lindsay Lohan. Plus, we got all the details on her 2004 legendary feud with Hilary Duff.
New York Girl
Lindsay Lohan was welcomed into the world by Dina and Michael Lohan on July 2, 1986, in the Bronx, NY. She is the eldest of four children: Lindsay, Michael Jr., Ali, and Cody. Throughout her early school years, Lindsay was a straight-A student and excelled in math and science. Back in those days, she didn’t play dumb to impress a boy. (That was a Mean Girl reference… I’m not being mean).
The adorable, freckle-faced child star started her acting career as a model at age three. The precious redhead worked for some big names like Abercrombie and Fitch Kids and Calvin Klein Kids. Before long, Lindsay Lohan landed commercial roles for brands like Wendy’s and Jell-O, where she was shown eating grape gelatin desserts.
Her Big Break
Lindsay got the opportunity to show her talent to the world when she landed not one but both lead roles in the hit Disney remake of the movie The Parent Trap. She played identical twin sisters, Hallie and Annie, and her performance was praised. What makes it even more impressive is that she was only 11 years old at the time.
Lindsay Lohan was actually offered the role of Penny in Inspector Gadget, but she turned it down, and the part ultimately went to Michelle Trachtenberg. In addition to The Parent Trap, Lindsay filmed some other Disney remakes, Herbie: Fully Loaded and Freaky Friday. She also starred in some Disney originals, like Confessions of a Teenage Drama Queen, Get a Clue, and Life-Size (starring Tyra Banks).
She Wanted to be Regina George
One of Lindsay’s most iconic roles is Cady Heron from the beloved chick-flick Mean Girls. But the actress originally auditioned for the part of Regina George. The role of the reigning Plastic was ultimately given to Rachel McAdams.
McAdams did a beautiful job playing the popular mean girl, and we can’t picture anyone but Lindsay as the 16-year-old girl who transferred to a public high school after being homeschooled in Africa her whole life. Both actresses are incredibly talented and made the movie the teenage classic that it has become.
Her Disney Roommate
As a Disney star, it only makes sense that Lindsay made friends with some other kids working with the network. She was even roommates with Raven Symone for a little while. The young actresses met at a fashion shoot and really hit it off.
Raven later revealed that Lindsay was never home: “She paid rent, and she was there probably three times.” But are you surprised? During this time, Lindsay was known for partying and constantly getting caught stumbling out of clubs by the tabloids. Although Lindsay had her share of issues, Raven defended her former friend on The View.
Her Singing Career
In addition to being a talented actress, the natural performer also embarked on a musical career, which is not uncommon for Disney stars. She recorded various songs that were featured on the soundtracks of the movies she starred in. She also released two albums and has spoken about a third one.
Lindsay was known for her emotional songs like Rumors and Confessions of a Broken Heart, which really helped humanize the actress. She also came out with a single called Bossy and was featured in a Duran Duran album.
Owning a Nightclub
Lindsay Lohan opened the Lohan Nightclub in Athens, Greece, back in 2015. She gave a significant amount of the profits to help refugees get their lives back on track. Reportedly, the actress moved to Greece because paparazzi are illegal there, and after what she’s been through with the tabloids, who can blame her?
Even though she stepped away from her former party lifestyle, when the club opened, she admitted how excited she was to be a partner in a nightclub. In 2019, she was featured in a reality show called Lindsay Lohan’s Beach Club, which follows some of the employees who went to work at the Mykonos location of the club for the summer.
Mean Girls Reunion?
In recent years, multiple classic shows and movies have returned with reboots and sequels, giving fans the feel-good nostalgic feeling they never knew they needed. Lindsay Lohan revealed that she has been determinedly pushing for a Mean Girls sequel.
Lindsay is excited and hopeful about it working out. She spoke out very candidly about it in interviews, saying that she is really trying to make this happen. So far, Mean Girls duo Tina Fey and Lorne Michaels haven’t confirmed anything… but they also haven’t denied it. Either way, my teenage heart can dream.
She Gets Allergies Too
On any given day, Linday’s favorite food is undoubtedly sushi. She loves it and is often spotted walking out of sushi spots by the paparazzi. However, she steers clear of blueberry muffins or pancakes because she is actually allergic to the berry. That sucks! Blueberries are so good.
Other than blueberries, Lohan is also allergic to horses. She has also suffered from asthma since she was a little girl. In fact, in 1996, she was hospitalized on Martha’s Vineyard while filming The Parent Trap because she had an asthmatic reaction to horses.
Way before Kim Kardashian was flooding out newsfeeds with selfies and became a reality show sensation, she was a regular socialite trying to get her foot in the Hollywood door. She worked as a closet organizer as well as a stylist for Lindsay Lohan and other notable names on the scene.
In the early 2000s, the paparazzi was obsessed with Lohan, Paris Hilton, and Britney Spears, and Kardashian worked for all three of them. No one expected her family’s reality show to last a whopping 20 seasons and for Kim to become a fashion icon in her own right.
Social Media Detox
Social media has become integrated into our daily lives, and Instagram can show your best (filtered) self, and well as your nasty mean side. For good or for bad, social media has taken over, and it becomes too much to handle at times, especially if you are a public figure with millions of followers.
For this very reason, Lohan deleted all her social media accounts. The actress, who was once known for sharing too much online, got rid of all her photos and videos and wiped all her accounts clean. However, in 2020, she turned to Instagram rebranding with a humbler approach to her life and career.
Redheads Have More Fun
You may not know this, but Lindsay auditioned for the role of Cora Cartmell in the incredibly successful Leonardo DiCaprio classic Titanic. At the time of casting, Lohan was an unknown actress, only eight years old, and was the number one choice for the role.
Unfortunately, James Cameron changed his mind at the last minute. The director was afraid that the actress’s red hair would confuse audiences into thinking she was related to the characters Ruth and Rose, who were also redheads. The role ultimately went to Alexandria Owens.
Keep Calm and Take Adderall
Lindsay Lohan deals with severe ADHD (attention-deficit/hyperactivity disorder). She takes Adderall prescriptions to help calm her down because she can’t sit still. As someone who also suffers from ADHD, I understand the struggle. Adderall is meant to help individuals when their ADHD starts to affect their life, but it contains addictive components and dangerous side effects.
According to Lohan, she has a prescription, unlike other girls, to take it in order to suppress their appetite and lose weight. She only takes it to relax her nerves. That doesn’t mean she didn’t battle addictions to other substances, but don’t worry, we will get to all that soon.
No Hangover for Her
Did you know that Lindsay Lohan nearly had a role in the hit comedy The Hangover? The actress almost starred as Jade, the hysterical stripper whose baby was found in the boys’ apartment the morning after their drunken night.
However, Lindsay didn’t want to take the role and turned it down. She probably had no idea the movie would be a huge box office success with two sequels. Heather Graham was cast instead, but I would have loved to have seen Lindsay in that movie. With her brilliant acting, she would have done an outstanding job.
The Best of Times, The Worst of Times
When Lindsay looks back at the happiest day of her life, it was the day she landed the double lead role as twin sisters Annie and Hallie in The Parent Trap. But the saddest day of her life was the day she saw her mother’s disappointed face after Lindsay had to turn herself into jail.
Lindsay had to serve time for violating her probation on a 2007 charge for drunk driving. She spent four out of her 12 days behind bars crying, feeling completely shocked and embarrassed about the whole situation. She was such a promising young star, and it’s difficult to pinpoint exactly when her life took such a drastic turn that landed her in the slammer.
Boys or Girls?
Lindsay made waves when she got into a relationship with DJ Samantha Ronson (2008 was a much different time). People immediately assumed Lindsay was into women… which made sense. However, she has since stated that she is straight. Wendy Williamsinterviewed the star on her drug use, Mean Girls sequel, and her sexuality.
When she was asked if she was sexually fluid, Lindsay said she wasn’t: “No, I like men.” When she was dating Ronson back in 2008, she was asked if she identified as bisexual and said, “maybe,” and then added that she doesn’t like labels. While discussing Samantha in more recent years, Lindsay claimed she was just living in LA and experimenting.
Learning From the Best
Brushing shoulders with Hollywood elites means you can get some exclusive advice from fellow celebrities. Lindsay is no exception, and although she is incredibly gifted in her craft, there is always room for improvement.
Lohan said the legendary Meryl Streep was so nice and encouraging and even advised her on what she needed to do differently in her acting. Her Freaky Friday costar, Jamie Lee-Curtis, advised the young star to get rid of her toxic relationships and stay away from people who are only friends with her because she is famous.
Old Hollywood Role Models
Lindsay’s top two all-time favorite films are Niagara and Kitten With a Whip, both respectively starring her favorite classic Hollywood darling, Marilyn Monroe. In fact, Lohan is such a huge Marilyn Monroe fan that she even made a tribute to the timeless icon.
Lohan posed nude in honor of Monroe’s 1962 legendary final photoshoot at the Hotel Bel-Air. Lohan revealed that in preparation for the shoot, she did 250 crunches the night before. What’s even more remarkable is that the iconic photographer, Bert Stern, took both sets of pictures: The original 1962 photos and Lohan’s 2008 set.
Following in Monroe’s iconic footsteps, Lohan posed nude for Playboy as the blonde inspiration. Considering Marilyn Monroe was the first-ever Playboy cover girl, this was a huge deal. The actress also earned an astonishing $1 million to strip down in the tasteful and pictorial shoot.
Lohan expressed that she feels the sexiest when she’s “naked and wearing Chanel No.5!” However, Lohan also admitted that she feels empowered and confident when she gets to be girly and womanly. She loves wearing lace or silk at night to make herself feel beautiful.
Year-Long Alcohol Break
It’s no secret that Lindsay Lohan has had her share of drunken nights. Prior to his death, Heath Ledger gave Lohan some health advice (or challenge, depending on how you look at it) and told her she should refrain from alcohol for one full year- which she did.
It was a much needed detox, and the break was eye-opening for Lindsay. The actress said she didn’t miss alcohol, and she felt good being more productive and focusing on her career. Ironically, and devastatingly, the world lost Ledger due to a substance overdose.
Don’t Drink and Drive
You are probably well-aware that Lindsay Lohan has been involved in cash crashes, but do you know how many? From 2005-2006 she was involved in six car accidents! The first was at a celebrity hotspot in Los Angeles called The Ivy. The collision was ruled by Lindsay’s fault, and she was charged with negligence.
Lohan was also arrested and charged a number of times. In 2007, she was arrested for two DUIs, and another two in 2012. This was separate from the four times her probation was revoked because she broke the law and somehow managed to skip getting arrested. In addition, she skipped a court date to go to Cannes, which set off her ankle monitoring bracelet. But that’s not all…
In the Slammer
The struggling actress failed a drug test and didn’t complete her community service. She has also been checked into rehab five times. When it comes to severe consequences for her actions, Lohan has been jailed six times but spent a total of fewer than two weeks behind bars.
She also spent 35 days on house arrest in connection with stealing a necklace. Needless to say, she encountered many run-ins with the law; between her various arrests and charges, the child star has spent 86% of her adult life on probation!
The Big Intervention
Tina Fey not only starred in Mean Girls, but she was the mastermind behind the movie. When she realized Lohan was on a downward spiral, she teamed up with Saturday Night Live producer Lorne Michaels and fellow cast members to stage an intervention. They were concerned and told her she should really re-evaluate the party lifestyle she was famous for.
They used the tragic deaths of former SNL stars John Belushi and Chris Farley as examples to put the reality of her situation in perspective. She was drinking all the time and frequently seen stumbling out of clubs. They didn’t want to see her on this dangerous path.
Learning From Her Mistakes… Kind Of…
Unfortunately, the beautiful actress didn’t learn her lesson. In 2011, a month after her rehab stint at the Betty Ford Clinic, she decided to steal a $5,000 necklace from a Jewelry store in LA. After she tried denying the theft allegations, video footage showed her wearing the expensive necklace.
Fortunately, it looks like she is taking a new life direction. The actress surprised everyone when she revealed that she’s been experimenting with modest fashion- pretty much the opposite of what she used to wear. She’s been following the modern dress guidelines and has been seen wearing a hijab. There was also a lot of talk about her attendance at London’s second Modest Fashion week.
Thank U, Not
Ariana Grande used her “Thank U, Next” music video to honor some of the most iconic chick flicks from the early 2000s, including Mean Girls. One of Grande’s friends was featured as Cady Heron, the character originated by Lohan. Many fans speculated about why Lohan herself wasn’t invited to join the cast for the video, and the actress thinks she knows the reason.
Lohan believes that it was probably too much to expect of them to fly her in from Dubai, where she currently lives. Either way, not being asked must have stung! Other films featured in Grande’s video were, Legally Blonde, Bring It On, and 13 Going on 30.
Lindsay Lohan’s Beach Club
After opening up her nightclub in Athens, Lohan launched beach clubs in two more locations, including Mykonos, which we briefly spoke about. MTV decided to create a reality show entitled Lindsay Lohan’s Beach Club, which would have followed Lohan trying to manage a rowdy American staff.
Unfortunately, the series was canceled after just one season. Reportedly, the show didn’t provide “enough drama.” It’s pretty ironic considering that drama and Lindsay go together like peanut butter and jelly. Shortly after the cancelation of the show, the Mykonos club closed down as well.
The Alcohol Truth
Despite her reputation and the countless headlines about her drug and alcohol abuse, Lindsay never actually had a sip of alcohol until she was 17. Surprisingly, she said she didn’t even like it, especially since the then high schooler got sick because of it.
To make matters worse, or to teach her a lesson, Lindsay’s mom made her go to sleep with vomit still on her clothing. That would certainly deter me from ever drinking again, and it worked for Lindsay… well, sort of. She didn’t touch alcohol again while she was still in high school. But, obviously, it was a whole other story after graduation.
Unless you have been living under a rock since 2010, you are aware of Amanda Bynes’s very public mental breakdown. When her legal battles were starting to pile up, fellow-child star Lindsay Lohan took the opportunity to kick her one-time rival when she was down.
Lohan was vocal about her frustration that Bynes wasn’t incarcerated after her troubles with the law, tweeting: “Why did I get put in jail and a Nickelodeon star had NO punishment(s) so far?” Come on, Lindsay, you’re really not one to talk. So much for supporting others who are in the same situation you were stuck in for years.
Kissing and Telling
It’s disappointing that Lindsay commented on Amanda’s breakdown and clear mental disorders. She should really look at her own behavior and focus on her own arrests. It’s not like Lohan didn’t make her way stumbling around Hollywood, and during her party days, she made her way around Hollywood men.
During one of her rehab stints, Lohan decided to make a list of every single person she ever had sexual relations with. The list was leaked in 2014, and a few famous and unexpected names were on there, including Adam Levine, Colin Farrell, James Franco, and Justin Timberlake.
Two Troubled Souls
Lindsay Lohan and Heath Ledger had a close bond before his untimely death. The details about the nature of their relationship are unclear, but Lindsay wrote in her diary that she was “in love” with Ledger in 2008, around the time of his heartbreaking death. On the exact day he died, the actress wrote about how she learned so much from him, stating that he was the love of her life.
She went on to reveal that he’s all she ever wanted, and she wants to hear his laugh and for him to hold her. Dina Lohan, Lindsay’s mom, confirmed that the two were seeing each other during that time. In fact, Ledger is one of the names on the list Lindsay wrote of the people she slept with.
Open Minded and Spiritual
Lindsay has expressed her interest in Islam, saying she’s a really spiritual person, open to learning anything. She revealed that in addition to studying the Quran, she spends a lot of her time in the Middle East. She currently lives in Dubai and visits Turkey. At the London Heathrow Airport, Lohan claims she was ethnically profiled while wearing a headscarf.
Apparently, an agent recognized Lohan’s name on her passport and asked her to remove the scarf. The agent later apologized, but the situation was uncomfortable. Lohan discussed the altercation and recognized how this is a common occurrence for women who wear head coverings for any reason.
That’ll Shake Things Up
Lohan was featured in an 8-part docuseries on Oprah Winfrey’s OWN cable network, entitled Lindsay. The show’s intention was to capture the actress getting back on her feet after her rehab stint in New York. The show wasn’t as fascinating as you would expect.
In fact, the series was pretty mild and basically showed Lindsay unpacking boxes for the most part. However, the last episode picked up traction for a heartbreaking reason. Lohan tearfully revealed that while filming the series, she had suffered a miscarriage and admitted that some of her behavior on the show had led to that horrible trauma.
Her Secret Sister
Lindsay claimed that Michael was an inadequate father on more than one occasion. As it turns out, he had a secret daughter, Ashley Horn, and didn’t reveal her existence until 2012. But this is where things get weird. Reportedly, Ashley went under the knife various times in order to look like her famous half-sister.
During an interview with In Touch Weekly, she said that she got her jaw, chin, and nose reshaped. In addition, she got fat injections to achieve her goal of looking like Lindsay back in her “good days.” Creepy.
Ashley later said that she was manipulated by the media and that looking like Lindsay was definitely not the reason she chose to get plastic surgery. She did agree with Lindsay about their father, saying, “I could never call Michael Lohan Dad. A dad is a person who is there for you and takes care of you.”
Lindsay also didn’t have the nicest things to say about Michael and told Vanity Fair that “I think my biggest focus for myself is learning how to continue to get through the trauma that my father has caused in my life.”
Keeps Organs in Her Fridge
In 2007, Lohan had to undergo an emergency appendectomy. When she got her appendix removed, she, well… took it home with her…. Apparently (and understandably), Lohan was worried that someone would try to sell it on eBay or the black market. Instead, she kept it in her home, safe and sound in the fridge.
While working together on Scary Movie 5, Lohan and Charlie Sheen became friends. Once he heard of Lohan’s money problems, the actor wrote her a $100,000 check to cover her tax debt. That’s definitely a good friend right there.
Needs Her Beauty Sleep
In 2002, Lohan appeared on Last Call with Carson Daly and admitted that when she attended the premiere of The Parent Trap, she fell asleep. But who could blame her? Playing two characters must have been exhausting. I guess it’s a good thing that she had time for a nap because she wasn’t just making movies.
Lindsay is more than just an on-screen sensation. She also took her talents to the stage. She was featured in the London production of David Mamet’s play Speed-the-Plow, playing a role originated by Madonna.
The Legendary Feud
Over the years, Lindsay has had her share of high-profile relationships with DJ Samantha Ronson, actor Wilmer Valderrama, and singer Aaron Carter. Her relationship with Carter caused a feud with her fellow Disney channel star, Hilary Duff, who had also dated the teenage heartthrob.
At the time, both actresses were teen icons at the height of their careers. Hilary was starring as the lead in the Disney series Lizzie McGuire, and she met Carter when he was a guest star on her show. The two shared an on-screen kiss on the Christmas episode, and they began dating on his 13th birthday.
Hilary vs. Lindsay
However, two years into Carter’s relationship with Hilary, he started dating Lindsay – AT THE SAME TIME! Afterward, Aaron told CNBC, “I was dating [Hilary] for like a year and a half, and then I just got a little bored, so I went, and I started getting to know Lindsay.” Gross!
Shortly after, Hilary and Aaron got back together, and he showed up to her big premiere for The Lizzie McGuire Movie. However, the couple split up again after Aaron reportedly cheated on her with someone else. This was just the beginning of their legendary rivalry.
Fighting Over Fake Boyfriends
The girls kept popping up at each other’s movie premieres. Hilary showed up at the red carpet for Freaky Friday, and Lindsay retaliated by attending the Cheaper by the Dozen premiere later that year. But things got crazier when Hilary was filming A Cinderella Story starring Chad Michael Murray.
Apparently, Lohan called her hunky Freaky Friday co-star, Chad, and talked trash about Hilary while he was playing her love interest. Things got awkward when Hilary brought Chad to Lindsay’s Freaky Friday premiere- the movie where Chad played Lindsay’s on-screen boyfriend. Lindsay couldn’t retaliate because Hilary reportedly banned her from the premiere of A Cinderella Story.
During a TRL appearance, Lindsay was put on the spot and asked to confess something about herself that she wants everyone to know. She confidently proclaimed, “I love you, Hilary Duff.” I think it’s safe to say that she didn’t really mean it and was poking fun at Hilary.
That wasn’t an isolated incident. During her Saturday night live monologue, Rachel Dratch dressed up as the blonde singer so they could make fun of her. Hilary was not impressed with how Lindsay treated her on SNL and said: “I’m not here to talk bad about her like she talks bad about me all the time.”
However, it reached a point where Hilary did feel the need to say something. She responded publicly to the rivalry, saying, “Sometimes I really hate Lindsay Lohan.” But then things got a little more personal. Hilary dated Joel Madden for a while.
During a Good Charlotte concert, Joel refused to sign an autograph for Lindsay’s eight-year-old brother Cody until Lindsay publicly apologized to Hilary. Considering Cody was not involved in the feud and was a little kid, it seems like things were taken a little too far.
The Rivalry Is Over
At this point, it looks like the feud is finally over. Lindsay and Hilary are both adults. Now that they are in their thirties, this whole thing is petty and immature. The ladies finally put this rivalry to rest, once and for all.
Hilary told People, “It’s over.” Lindsay showed up to Hilary’s album release party for Dignity. She even referred to Lindsay as “really fun.” She went on to say, “We were hanging out the other night, and she’s a nice girl.” So, yes, this legendary feud is finally over!