Lindsay Dee Lohan (born July 2, 1986) is an American actress, singer, model, and fashion designer.
During childhood, Lohan was signed to Ford Models and appeared as a regular on Another World. Her film debut was in Disney's blockbuster The Parent Trap (1998). The film's commercial success lead to Lohan starring in Disney's television films Life-Size (2000) and Get a Clue (2002), and alongside Jamie Lee Curtis in the theatrical release Freaky Friday (2003), where she also debuted her radio single "Ultimate". Lohan became a teen idol after starring in the sleeper hit Mean Girls (2004). Her work success lead to growth in her celebrity, making her a frequent focus of the media. Her recording contract with Casasblanca resulted in commercial albums Speak (2004) and A Little More Personal (Raw) (2005), which were certified platinum and gold, respectively. Following the negative critic response to Herbie: Fully Loaded (2005) and Just My Luck (2006), Lohan focused on mature roles in independent movies A Prairie Home Companion (2006), Bobby (2006) and Chapter 27 (2007), which earned her praise. In 2007, Lohan was subject to intensive media scrutiny after two driving under the influence incidents that lead to probation. During this time, her attending rehabilitation facilities three times resulted in the loss of several movie deals.
During the late 2000s, she focused on her career in the fashion industry by taking on more modeling gigs and launching the clothing line 6126. She returned to acting with television film Labor Pains (2009) and Machete (2010). In the early-2010s, Lohan received additional rehabilitation treatment and faced legal problems stemming from misdemeanors and probation violations. While facing difficulty gaining role in this period, she still received parts in Liz & Dick (2012) and The Canyons (2013). In 2014, she had a highly publicized tell-all interview with Oprah. Following this, she starred in an OWN docu-series titled Lindsay, which followed her recovery. This was the first time she had been probation free for nearly 8 years. She made her stage debut in the London West End production of Speed-the-Plow in 2015.
Based in London, England, Lohan is currently working on revitalizing her career, with upcoming projects including a starring role in the independent film The Shadow Within (2018) and a recurring role on the British sitcom Sick Note, starting in 2018. She has also stated intentions to begin humanitarian work for Women's rights and Saudi Arabia-affiliated causes.
Lindsay Lohan was born on July 2, 1986, in The Bronx, New York City, and grew up in Merrick and Cold Spring Harbor on Long Island, New York. She is the eldest child of Dina and Michael Lohan. Her father, a former Wall Street trader, has been in trouble with the law on several occasions, while her mother is a former singer and dancer. Lohan has three younger siblings, all of whom have been models or actors: Michael, Jr., who appeared with Lohan in The Parent Trap, Aliana, known as "Ali," and Dakota "Cody" Lohan. Lohan is of Irish and Italian heritage, and she was reared as a Catholic. Her maternal antecedents were "well known Irish Catholic stalwarts" and her great-grandfather, John L. Sullivan, was a co-founder of the Pro-life Party in Long Island. Lohan attended Cold Spring Harbor High School and Sanford H. Calhoun High School, where she did well in science and mathematics, until grade 11, when she started homeschooling. Lohan is a natural red head.
Lohan's parents have a turbulent history. They married in 1985, separated when she was three, and later reunited. They separated again in 2005 and finalized their divorce in 2007.
Lohan began her career as a child model with Ford Models at the age of three. She modeled for Calvin Klein Kids and Abercrombie, and appeared in over 60 television commercials for brands like Pizza Hut and Wendy's, as well as a Jell-O spot with Bill Cosby. By the age of 10, when Lohan played Alexandra "Alli" Fowler in the television soap opera Another World, Soap Opera Magazine said she was already considered a show-business veteran.
Lohan remained in the role for a year, before leaving to star in Disney's 1998 family comedy The Parent Trap, a remake of the 1961 movie. She played dual roles of twins, separated in infancy, who try to reunite their long-divorced parents, played by Dennis Quaid and Natasha Richardson. The film earned $92 million worldwide, and received largely positive reviews. Lohan received unanimous acclaim for her debut performance. Critic Kenneth Turan called Lohan "the soul of this film as much as Hayley Mills was of the original," going on to say that "she is more adept than her predecessor at creating two distinct personalities." The film won Lohan a Young Artist Award for best performance in a feature film as well as a three-film contract with Disney. At the age of 14, Lohan played Bette Midler's daughter in the pilot episode of the short-lived series Bette, but she resigned her role when the production moved from New York to Los Angeles. She also starred in two Disney television movies: Life-Size alongside Tyra Banks in 2000, and Get a Clue in 2002.
Next Lohan starred alongside Jamie Lee Curtis in the 2003 remake of Disney's family comedy Freaky Friday, playing a mother and daughter who switch bodies and have to take on each other's roles. At Lohan's initiative, her character was rewritten and changed from a Goth style to be more mainstream. Her performance was once again met with significant praise. Critic Roger Ebert wrote that Lohan "has that Jodie Foster sort of seriousness and intent focus beneath her teenage persona." Freaky Friday earned Lohan the award for Breakthrough Performance at the 2004 MTV Movie Awards and, as of 2015, it remained her most commercially successful film, earning $160 million worldwide as well as an 88 percent approval rating on Rotten Tomatoes.
In 2004, Lohan had two lead roles. The first film, Disney's teen comedy Confessions of a Teenage Drama Queen, earned a domestic box office total of $29 million, with Brandon Gray of Box Office Mojo commenting that it was "well above expectations as it was strictly for young girls." But the film did not meet with critical acclaim. Robert K. Elder of the Chicago Tribune wrote that "though still a promising star, Lohan will have to do a little penance before she's forgiven for Confessions." Her second lead role that year, in the teen comedy Mean Girls, marked Lohan's first movie independent of Disney. Based in part on the non-fiction book Queen Bees and Wannabes, the film stars Lohan as a previously homeschooled 16-year-old learning to navigate the social cliques of a public high school. It was a critical and commercial success, grossing $129 million worldwide and, according to Brandon Gray, "cementing her status as the new teen movie queen." Mick LaSalle from the San Francisco Chronicle wrote that "Lohan is sensitive and appealing, a solid locus for audience sympathy." David Rooney from Variety said that "Lohan displays plenty of charm, verve and deft comic timing." Lohan received four awards at the 2004 Teen Choice Awards for Freaky Friday and Mean Girls, including Breakout Movie Star. Mean Girls also earned her two awards at the 2005 MTV Movie Awards. With Mean Girls, Lohan's public profile was raised significantly. Vanity Fair described how she became a household name. Paparazzi began following her and her love life and partying became frequent targets of gossip sites and the tabloid media. Following Mean Girls, which was scripted by former "Not Ready For Prime Time Actress" Tina Fey and featured several other veterans of Saturday Night Live's "Not Ready For Prime Time Company," Lohan hosted the show three times between 2004 and 2006. In 2004, when Lohan was 17, she became the youngest host of the MTV Movie Awards and in 2006 she hosted the 2006 World Music Awards.
Lohan returned to Disney in 2005, starring in the comedy Herbie: Fully Loaded, the fifth film in the series with the anthropomorphic car Herbie. Fully Loaded earned $144 million worldwide, but it received mixed reviews. Stephen Holden of The New York Times called Lohan "a genuine star who ... seems completely at home on the screen", while James Berardinelli wrote that "as bright a starlet as she may be, Lohan ends up playing second fiddle to the car." While shooting the film in 2004, Lohan was hospitalized with a kidney infection brought on by stress in her personal life and from recording her first album while the film was in production, prompting Vanity Fair to label it Lohan's "first disastrous shoot.". She also guest-starred in an episode of That '70s Show, of whose cast Wilmer Valderrama, her boyfriend at the time, was a regular member. According to Vanity Fair, the breakup with Valderrama contributed to Lohan's issues during the Herbie shoot. In 2005, Lohan became the first person to have a My Scene celebrity doll released by Mattel. She also voiced herself in the animated direct-to-DVD film My Scene Goes Hollywood, based on the series of dolls.
Following Mean Girls, Lohan spent several years living out of hotels in Los Angeles, of which two years were spent at the infamous Chateau Marmont, where comedy actor John Belushi, himself a former "Not Ready For Prime Time Actor," had died. In late 2007, after settling down in a more permanent residence, she explained that she "didn't want to be alone" but that "it wasn't a way of life ... not very consistent." She had a series of car accidents that were widely reported, in August 2004, October 2005, and November 2006, when she suffered minor injuries because a paparazzo who was following her for a photograph hit her car.
Lohan's next widely released film, the romantic comedy Just My Luck, opened in May 2006 and, according to Variety, earned her over $7 million. The opening weekend box office takings of $5.7 million "broke lead actress Lindsay Lohan's winning streak" according to Brandon Gray. The film received poor reviews and earned Lohan her first Golden Raspberry nomination for Worst Actress. Following Just My Luck, Lohan focused on smaller roles in more mature, independent movies. Robert Altman's ensemble comedy A Prairie Home Companion, based on humorist Garrison Keillor's works, in which Lohan co-stars with Meryl Streep and Lily Tomlin, had a limited release in June 2006. Peter Travers wrote for Rolling Stone that "Lohan rises to the occasion, delivering a rock-the-house version of 'Frankie and Johnny.'" Co-star Streep said of Lohan's acting: "She's in command of the art form" and "completely, visibly living in front of the camera." The Emilio Estevez ensemble drama Bobby, about the hours leading up to the Robert F. Kennedy assassination, was released in theaters in November 2006. Lohan received favorable comments for her performance, particularly a scene alongside Sharon Stone. As part of the Bobby ensemble cast, Lohan was nominated for a Screen Actors Guild Award. In 2006, Lohan attended Alcoholics Anonymous meetings.
Lohan's next appearance was in Chapter 27 as a John Lennon fan who befriends Mark David Chapman, played by Jared Leto, on the day he murders Lennon. Filming finished in early 2006, but the film was not released until March 2008 due to difficulties in finding a distributor. In May 2007, the drama Georgia Rule was released. In the film, Lohan portrays an out-of-control teenager whose mother (Felicity Huffman) brings her to the house of her own estranged mother (Jane Fonda). Owen Gleiberman of Entertainment Weekly wrote that "Lohan hits a true note of spiteful princess narcissism." During filming in 2006, Lohan was hospitalized, her representative saying "she was overheated and dehydrated." At the time Lohan was going through a breakup with Hard Rock Cafe heir Harry Morton, which contributed to her problems on the set, according to Allure. In a letter that was made public, studio executive James G. Robinson called Lohan "irresponsible and unprofessional." He mentioned "various late arrivals and absences from the set" and said that "we are well aware that your ongoing all night heavy partying is the real reason for your so-called 'exhaustion.'" In 2007, Lohan was cast in the film Poor Things. But in May of that year, she was arrested on a charge of driving under the influence of alcohol (DUI.) The film's producers initially voiced support, and production was put on hold, as Lohan entered the Promises Treatment Center rehabilitation facility where she stayed for 45 days. She ultimately lost the Poor Things part. In July, less than two weeks out of rehab, Lohan was arrested a second time on charges of possession of cocaine, driving under the influence and driving with a suspended license. In August, Lohan pleaded guilty to misdemeanor cocaine use and driving under the influence and was sentenced to an alcohol education program, community service, one day in jail, and was given three years probation. Lohan released a statement in which she said "it is clear to me that my life has become completely unmanageable because I am addicted to alcohol and drugs." The same month she entered the Cirque Lodge Treatment Center in Sundance, Utah for a third stint at rehabilitation, staying for three months until her discharge in October. In November Lohan served 84 minutes in jail. A sheriff spokesman cited overcrowding and the nonviolent nature of the crime as reasons for the reduced sentence.
In early January 2007, production on the film I Know Who Killed Me was put on hold when Lohan underwent appendix surgery. Lohan admitted herself to the Wonderland Center rehabilitation facility for a 30-day stay, though she continued shooting the film, returning to the facility at night. Shortly thereafter, Lohan withdrew from a film adaptation of Oscar Wilde's A Woman of No Importance, her publicist stating that Lohan needed to "focus on getting better." Lohan was replaced in The Edge of Love in April 2007, shortly before filming was to begin, with the director citing "insurance reasons" and Lohan later explaining that she "was going through a really bad time then."
In the wake of her second DUI arrest, Lohan withdrew from a scheduled appearance on The Tonight Show with Jay Leno in which she had been due to promote I Know Who Killed Me, a low-budget psychological horror-thriller in which she stars as a stripper with a dual personality. The film premiered in July 2007 to what Entertainment Weekly called "an abysmal $3.5 million." It earned Lohan dual Golden Raspberry awards for Worst Actress, with Lohan coming first and second, tying with herself. Hollywood executives and industry insiders commented that it would be difficult for Lohan to find employment until she could prove that she was sober and reliable, citing possible issues with securing insurance.
In May 2008, Lohan made her first screen appearance since I Know Who Killed Me, on ABC's television series Ugly Betty. She guest starred in four episodes as Kimmie Keegan, an old schoolmate of the protagonist Betty Suarez. Articles about Lohan have appeared in various men's magazines. She was voted No. 10 on the list of "100 Sexiest Women" by readers of FHM in 2005, No.13 in 2006, No.30 in 2007, and No.41 in 2008, while Maxim placed her third on its "Hot 100" list in 2006 and first in 2007. Lohan has been the face of Jill Stuart, Miu Miu, and Dooney & Bourke, as well as the 2008 Visa Swap British fashion campaign. She was also the face of Italian clothing company Fornarina for its Spring/Summer 2009 campaign. Lohan has a long-lasting fascination with Marilyn Monroe going back to when she saw Niagara during The Parent Trap shoot. In the 2008 Spring Fashion edition of New York magazine, Lohan re-created Monroe's final photo shoot, known as The Last Sitting, including nudity, saying that the photo shoot was "an honor." The New York Times critic Ginia Bellafante found it disturbing, saying "the pictures ask viewers to engage in a kind of mock necrophilia. ... [and] the photographs bear none of Monroe's fragility." In 2008, Lohan launched a clothes line, whose name 6126 was designed to represent Monroe's birth date (June 1, 1926). The line started with leggings, before expanding to a full collection, covering 280 pieces as of April 2010. In April 2009, Lohan released a self-tanning spray under the brand name Sevin Nyne in collaboration with Sephora. In September 2009, Lohan became an artistic adviser for the French fashion house Emanuel Ungaro. A collection by designer Estrella Archs with Lohan as adviser was presented in October, receiving a "disastrous" reception, according to Entertainment Weekly and New York. Lohan left the company in March 2010.
In the comedy Labor Pains, Lohan plays a woman who pretends to be pregnant. During the shoot, Lohan's manager worked with the paparazzi to encourage the media to show her working, as opposed to partying. It was originally planned for a theatrical release, but instead appeared as a TV movie on the ABC Family cable channel in July 2009, "a setback for the star" according to Variety. The premiere received 2.1 million viewers, "better-than-average" for the channel according to E! Online. Alessandra Stanley of The New York Times wrote that "this is not a triumphant return of a prodigal child star. ... [Labor Pains] never shakes free of the heavy baggage Ms. Lohan brings to the role." Lohan was a guest judge on US TV style contest Project Runway sixth-season premiere episode, which aired in August 2009.
In October 2009, Lohan's DUI probation was extended by an additional year, following several instances in which she failed to attend the court-ordered substance abuse treatment classes.
Lohan narrated and presented the British television documentary Lindsay Lohan's Indian Journey, about human trafficking in India. It was filmed during a week in India in December 2009, and transmitted on BBC Three in April 2010. The BBC was criticized for having hired Lohan, and while reviewers called the documentary compelling, they also found Lohan's presence to be odd and distracting. Lohan said: "I hope my presence in India will bring awareness to the really important issues raised in making this film." In April 2010, Lohan was let go from the film The Other Side where she had been set to star, with the director saying she was "not bankable." In May 2010, Lohan traveled to the Cannes Film Festival to promote the biographical drama Inferno. She was set to star as the lead, adult-film performer Linda Lovelace, but was later replaced while in court mandated rehab. Because she was in Cannes, Lohan missed a mandatory DUI progress hearing. A bench warrant was issued for her arrest which was rescinded after she posted bail. A judge determined that Lohan had violated the terms of her probation by missing several mandatory classes and meetings. She was sentenced to 90 days in jail, followed by 90 days of inpatient rehab treatment. However, Lohan served only 14 days of the jail sentence, due to overcrowding. She then entered an inpatient rehabilitation facility, from where she was released after only 23 days.
In June 2010, Lohan was the subject of a fashion shoot in the photographer docu-series Double Exposure on Bravo. Robert Rodriguez's action exploitation film Machete opened in September 2010. In the film, Lohan's character takes drugs, is naked in much of her appearance, and later dons a nun's habit while toting a machine gun. Its critical reviews were mixed. The Washington Post described her character as "a campier, trampier version of herself – or at least her tabloid image." Premiere.com said she was "terrible" while Variety called it "her best work in some time." Because of her rehabilitation and legal engagements, Lohan did not participate in promotion of the movie. Lohan filmed a sketch where she is dressed as Marilyn Monroe for Inappropriate Comedy in 2010. The film had issues finding a distributor and was not released until 2013, when it was met with poor box office and critical reception. Lohan appeared on the October 2010 cover of Vanity Fair. She told the magazine: "I want my career back" and "I know that I'm a damn good actress."
In September 2010, Lohan's probation was revoked following a failed drug test. She spent part of the day in jail before being released on bail. A few days later, she entered the Betty Ford Center, a drug and alcohol treatment center, where she remained on court order for three months until early January 2011. In February 2011, Lohan was charged with the theft of a necklace reported stolen from a jewelry store the month before. She was sentenced to community service and 120 days in jail for misdemeanor theft and probation violation, to which she pleaded no contest. Due to jail overcrowding, Lohan served the sentence under house confinement, wearing a tracking ankle monitor for 35 days. In November, Lohan was found to have violated the terms of her probation by failing to perform the required community service. She was sentenced to additional community service and 30 days in jail, of which she served less than 5 hours due to overcrowding.
Lohan appeared in the January/February 2012 issue of Playboy magazine, in a shoot inspired by a nude pictorial of Marilyn Monroe from the first issue of the magazine. Editor Hugh Hefner said Lohan's issue was "breaking sales records." Lohan had not appeared on Saturday Night Live since 2006, when she hosted the show for the fourth time in March 2012. Her appearance received mixed to negative reviews. Critics appreciated the self-deprecating references to her personal troubles, but also commented that she largely played a supporting role. The episode had the second highest ratings of the season with 7.4 million viewers. In May 2012, Lohan appeared briefly, as a celebrity judge, on the television series Glee, in the episode "Nationals." Lohan stars as a surfer in the art film First Point by artist Richard Phillips. It debuted at Art Basel in June 2012 and features a score by Thomas Bangalter from Daft Punk. Comments from critics on Lohan's work were mixed.
Lohan starred as Elizabeth Taylor in the biographical made-for-TV movie Liz & Dick, which premiered on the Lifetime cable channel in November 2012. Reviews of Lohan's performance were largely, but not unanimously, negative. The Hollywood Reporter said she was "woeful" while Variety called her "adequate." Entertainment Weekly described the premiere ratings of 3.5 millions as "a little soft." On way to the Liz & Dick set in June 2012, Lohan was in a car accident, where she sustained minor injuries and which caused a delay in production. During the production, paramedics were called to Lohan's hotel room, treating her for exhaustion and dehydration.
In March 2013, Lohan pleaded no contest to misdemeanor charges stemming from the June 2012 car accident; reckless driving and providing false information to a police officer. She was sentenced to community service, psychotherapy and lockdown rehabilitation. Her probation was also extended for another two years. Between May and July 2013 Lohan spent 90 days in rehabilitation.
In April 2013, the horror comedy Scary Movie 5 was released, where Lohan appears as herself alongside Charlie Sheen in the opening sketch. While the movie itself was panned by critics, a few reviewers found Lohan's and Sheen's to be one of the better scenes. The same month Lohan guest-starred as herself in an episode of Sheen's comedy series Anger Management.
In August 2013, just days after Lohan left rehab, The Canyons was released, an independent erotic thriller directed by Paul Schrader and written by Bret Easton Ellis. It was made on a low budget, most of which was gathered through online fund raiser Kickstarter. Lohan received $100 a day and a share of the profits, and she was also credited as a co-producer. The New York Times Magazine described Lohan as difficult to work with, and the shoot as fraught with conflict between Lohan and Schrader. Lohan and her co-star, adult-film actor James Deen, portray an actress and a producer in a volatile relationship. Reviews for the film were generally poor, but several critics praised Lohan's performance. The New Yorker said she was "overwrought and unfocused" while Variety called her "very affecting" and Salon described her as "almost incandescent." The same month Lohan filled in for Chelsea Handler as host of the cable talk show Chelsea Lately. She received mostly positive reviews for her appearance and the show garnered its best ratings of the year.
The 8-part docu-series Lindsay was transmitted in March and April 2014 on Oprah Winfrey's OWN cable network. The series followed Lohan's life and work as she moved to New York City after leaving rehab. In the final episode, Lohan said that she had had a miscarriage which had interrupted filming of the series. The premiere had 693,000 viewers, described as "so-so" by The Hollywood Reporter. The ratings then slipped and the finale only had 406,000 viewers. New York Daily News called the series "surprisingly routine," Variety described it as boring, while Liz Smith said it was "compelling" and "usually painful to watch." In April 2014, Lohan guest-starred in an episode of the CBS sitcom 2 Broke Girls. In July 2014, she filed a lawsuit against Rockstar Games claiming elements in the video game Grand Theft Auto V were influenced by her image, voice and clothing line without permission. Rockstar responded in court papers that sought a dismissal of the case, saying that the case was frivolous and filed for publicity purposes.
Lohan made her stage debut in October 2014, starring in the London West End production of David Mamet's Speed-the-Plow, a satire about the movie business. She portrayed Karen, the secretary of a Hollywood executive, in a role originally played by Madonna. Reviews of Lohan's performance were mixed, with the Associated Press describing critical reception overall as "lukewarm." The Stage said she was "out of her league" while The Times wrote that she "can act a bit" and The Guardian said she "holds the stage with ease." In December 2014, the free-to-play video game app Lindsay Lohan’s The Price of Fame was released for the iOS and Android operating systems. Polygon said it was "funny, trashy and surprisingly self-aware" while Vulture called it "a crappy knockoff of Kim Kardashian: Hollywood." In May 2015, a judge ended Lohan's probation after she completed the community service that resulted from her 2012 reckless driving, making it the first time in nearly 8 years that she was probation free. She will appear as Katerina West for the second season of the UK comedy series Sick Note.
In June 2017, Lohan announced she was starting a lifestyle site called Preemium, which subscribers could access for $2.99 a month.
Lohan had planned on releasing an album in the summer of 2001, according to her official website, llrocks.com. No album was released in 2001, but Lohan had begun recording demo tracks with Emilio Estefan, Jr.. He and his wife, Gloria Estefan, signed Lohan to a five-album production deal in September 2002. "I am extremely excited to be working with Emilio. I am surrounded by a group of very talented people whom have made me feel like part of their family," Lohan said to the press. Also in September, Lohan landed the role as the daughter in Disney's remake, Freaky Friday, which required her to learn how to play the guitar and to sing. Lohan recorded a song for the film, "Ultimate," which was released to Radio Disney to help promote the film. The song peaked at #18 on Radio Disney's Top 30. Lohan announced that the song was separate from her singing career, since many teen idols such as Hilary Duff and Raven-Symoné were expanding their careers from acting to singing. In 2003, Lohan recorded four songs including a Radio Disney hit, "Drama Queen (That Girl)," that were released for the soundtrack to Lohan's film, Confessions of a Teenage Drama Queen.
Lohan began writing the tracks on her album in April 2004. "I write a lot of lyrics and I'm involved in the producing process, because it's like, if I'm singing it, I want it to be something that I can relate to," Lohan said. "I'm just trying to feel it out and see where it goes. I'm playing guitar and I also love to dance, so [the music will be] somewhere along the lines of hip-hop and rock." She had begun working with Diane Warren and Randy Jackson, who were going to help write and produce her album. Diane Warren wrote the song, "I Decide," for Lohan which was originally going to be on her album. When Lohan decided not to collaborate with Warren and Jackson, "I Decide" was instead released on the soundtrack to the film The Princess Diaries 2: Royal Engagement and on to Radio Disney.
Lohan's debut album, Speak, was released in the United States on December 7, 2004. The album was the first high-seller from Casablanca Records in several years, selling 1,000,000 units in the United States. The album received mostly negative reviews, with critics commenting that Lohan "isn't a bad singer, but not an extraordinary singer either." In the United States, the album peaked at number four on the Billboard 200, selling 261,762 copies in its first week. In Germany the album debuted at the #53 position and took four weeks to complete its chart run. The first two singles from Speak, "Rumors" and "Over," were both successes, with "Over" topping the Bubbling Under Hot 100 Singles where it stayed for three weeks. The song also did well internationally in countries such as Australia, Ireland, and the United Kingdom. "Rumors" peaked at #6 on the Bubbling Under Hot 100 Singles chart and also did well in Australia and Germany, where it reached #14. The music video for "Rumors" was nominated for "Best Pop Video" at the 2005 MTV Video Music Awards. Both songs received heavy airplay on MTV's Total Request Live. The final single, "First," was released to help promote Lohan's film, Herbie: Fully Loaded. The song earned small success in Australia and Germany. Lohan promoted the album by performing the songs in a number of live appearances. Plans for a tour in Taiwan were planned, but were later scrapped.
Lohan's second album, A Little More Personal (Raw), was released in December 2005. It peaked at number 20 on the Billboard 200 chart, and was eventually certified Gold. Lohan co-wrote most of the songs on the album, which received a mixed critical response. Slant Magazine called it "contrived ... for all the so-called weighty subject matter, there's not much meat on these bones." Lohan herself directed the music video for the album's only single, "Confessions of a Broken Heart (Daughter to Father)," which features her sister Ali Lohan. The video is a dramatization of the pain Lohan said her family suffered at the hands of her father. It was her first song to chart on the Billboard Hot 100, peaking at number 57.
Following a switch to Universal Motown, Lohan began working on a third album, tentatively titled Spirit in the Dark, in late 2007. In May 2008, the single "Bossy" was released onto digital outlets, which reached number one on the US Billboard Hot Dance Club Play chart. The single was meant to serve as the lead single from the album. Later that year, Lohan said that work on the album had stalled and that she wanted to avoid the stress of working on movies and music at the same time.
In 2015, the English band Duran Duran announced that Lohan had been featured on the song "Dancephobia" from their upcoming fourteenth studio album, Paper Gods. In June 2016, Lohan confirmed her intentions for recording and releasing her third studio album during an online video chat with her fans. Lohan confirmed that she owed her record label one final album, as per her contract, and would only release music once it would not upset her younger sister, Ali, who is also pursuing her own music career.
In July 2007, Lohan's home was burgled by the Bling Ring, a group of fashion-motivated burglars whose ringleader considered Lohan to be their ultimate conquest. Video surveillance of the burglary recorded at Lohan's home played a large role in breaking the case.
During the 2008 US presidential campaign, Lohan offered her services to Barack Obama's Democratic election effort, but was declined. In a blog post, Lohan criticized the media and then Republican Vice Presidential candidate Sarah Palin for not focusing on policy, and attacked Palin's positions on homosexuality, birth control and abortion. Lohan had previously expressed an interest in going to Iraq, during the Iraq War in 2006, on a USO tour with Hillary Clinton. In the 2012 presidential election, Lohan supported Republican candidate Mitt Romney, something that prompted ABC News to call her a "political turncoat". Only weeks later, she tweeted words supportive of Obama.
Speaking about her sexual orientation, Lohan said that she was not a lesbian. When asked if she was bisexual in 2008, she responded "Maybe. Yeah," adding, "I don't want to classify myself." However, in a 2013 interview, she said, "I know I’m straight. I have made out with girls before, and I had a relationship with a girl. ... I think I was looking for something different."
In April 2016, it was reported that Lohan was studying Islam after she was spotted carrying a copy of the Quran; Lohan confirmed the reports herself.
In October 2017, Lohan received scrutiny for defending Harvey Weinstein, whom she worked with on several films, on Instagram and saying that his wife Georgina Chapman should stay with him. Weinstein had been accused of sexual harassment and sexual assault.
Lohan reportedly dated fellow teen star Aaron Carter between 2000 and 2001. The relationship garnered media attention with reports of a love triangle between Lohan, Carter, and actress and singer Hilary Duff. Lohan began dating actor Wilmer Valderrama in 2004. She also guest-starred in an episode of That '70s Show, where Valderrama was a regular. After their break-up, Lohan wrote her second single, "Over", about the experience. Lohan dated Hard Rock Cafe heir Harry Morton in 2006. In May 2007, Lohan dated British TV personality Calum Best. While in rehab in July 2008, Lohan met and dated snowboarder Riley Giles. Lohan dated DJ Samantha Ronson in 2008 and 2009. She co-hosted club events with Ronson and accompanied her when she was DJ-ing. In April 2009, following her breakup with Ronson, Lohan appeared in a dating video spoof on the comedy website Funny or Die. It was viewed 2.7 million times in the first week and received favorable comments from the media. As of 2016, her love interest and fiancé was London based Russian millionaire Egor Tarabasov, a real estate agency owner, called Home House Estates and son of Dmitry Tarabasov.They reportedly broke up in mid 2017 with Lindsay accusing Egor of abuse and him accusing her of stealing £24,000 worth of his belongings.
Lohan spoke about her turbulent childhood in 2007, the same year her parents finalised their divorce: "I feel like a second parent in the sense that I helped raise my family...I was put between my mother and father a lot." Despite the conflicts, Lohan spoke very fondly of her family. However, in 2007, 2008, and 2009 she admitted that she had cut off contact with her father, describing his behavior as unpredictable and hard to deal with.