1989

An Early Start

Ford Modeling Agency signs on 3-year-old Lohan. She appears in more than 60 commercials, including spots for Pizza Hut, Wendy's and Jell-O, with Bill Cosby. She also models for Abercrombie & Fitch Kids and Calvin Klein Kids. In 1996, she lands a TV role as Alli Fowler in the soap opera Another World and plays the character for a year.

1998

Lindsay Lohan

July 20

Lindsay: Double-Time

Lohan plays identical twins Hallie and Annie in Disney's The Parent Trap, earning her a Young Actress Award for Best Leading Actress in a Feature Film. Director Nancy Meyers likens Lohan to a young Diane Keaton, an actress "gifted as a comedian but who doesn't know it." Lohan signs a three-movie contract with Disney. Next, she stars in Disney's Life Size with Tyra Banks and Get a Clue.

2002

Lindsay Lohan

January

Teen Queens Clash

Lohan dates singer Aaron Carter, prompting reports of tension between her and fellow teen queen Hilary Duff, Carter's on-and-off again girlfriend who dated him prior to Lohan. Both actresses deny any beef, with Duff telling PEOPLE in 2005: "I have nothing to say about [the spat]. I don't even know her."

September

Becoming an Actress-Singer

Following her dream of becoming a singer, Lohan signs a five-album production deal with Grammy award-winning producer Emilio Estefan. Two years later, Lohan signs a recording contract with Tommy Mottola's Casablanca Records. Mottola, who was the driving force behind Mariah Carey and Jennifer Lopez's music careers, says to PEOPLE, "She is like rapid-fire – really quick, really smart."

2003

Lindsay Lohan

August 04

Lohan Gets Freaky

After a five-year delay, Freaky Friday with Lohan and Jamie Lee Curtis is released. Lohan plays a teen who switches bodies with her mom. She also contributes to the movie soundtrack. It rakes in more than $110 million and Lohan wins the MTV Movie Award for Best Breakthrough Female.

2004

Lindsay Lohan

April 19

From Mean Girl to "It" Girl

The high school flick Mean Girls starring Lohan and Rachel McAdams scoops up $86 million at the box office. The film, written by 30 Rock and former SNL star Tina Fey, pushes Lohan into the spotlight and confirms her as a bankable star. PEOPLE names the stunning redhead in its 50 Most Beautiful issue.

Lindsay Lohan

May

Lohan's 'First Love'

Lohan, 17, reveals to PEOPLE the reason why she's currently single: "It's because I'm 17 and I like 24-year-olds – and that's illegal." But, Lohan soon finds herself a dateable 24-year-old, stepping out with That '70s Show star Wilmer Valderrama. Lohan's mom, Dina, later calls Valderrama her daughter's "first love." In November, just weeks after Lohan makes a cameo appearance on Valderrama's show, reps confirm the two have broken up.

Lindsay Lohan

May 31

Blowing Up

Lohan's partying isn't the only tabloid-grabbing item; the teen star's curvier figure is also under the media's watch. Reports surface that Lohan has had breast implants. "It's retarded," says Lohan of the notion that she had plastic surgery. "I'm 17 years old. My mother would never let me." Still, the actress admits that she's flattered: "I'm glad people think I have a nice chest." When Lohan hosts Saturday Night Live for the first time that month (she hosts again in 2005 and 2006), she makes light of her suddenly large chest.

Lindsay Lohan

December 07

Singing Sensation

Lohan releases her first album, Speak, which goes platinum. Her single "Rumors," about a teen celebrity trying to keep her private life out of the spotlight, goes gold.

2005

Lindsay Lohan

April

The Incredible Shrinking Actress

Lohan's noticeably thinner frame attracts press scrutiny, but she attributes her weight loss to a new workout regimen. "There's a lot of pressure [to be thin]," she tells Access Hollywood. In 2007, once her curvier figure returns, she tells Allure, "When I lost weight, everything reduced and changed. Then I gained weight again, and I was like, Wow, the breasts are really back."

Photo Credits

BIOGRAPHY (top to bottom): Walt Disney/Everett; Lenny Furman/South Beach Photos; Ron Batzdorff/Disney; Chris Weeks/Wireimage; Matt Baron/BEImages; Shawn/X 17

Edited by Julia Wang

Lindsay Lohan

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