1993

Jessica Simpson

Mousketears

After making it to the last 13 candidates for Disney's The New Mickey Mouse Club, 12-year-old Simpson chokes in the final audition. She loses to Justin Timberlake, Britney Spears, Christina Aguilera and Ryan Gosling (left). "I froze and forgot everything," she tells PEOPLE in 2000.

1999

Jessica Simpson

January

Sweet Kisses for Nick

Simpson meets 98 Degrees lead singer Nick Lachey at a Teen People party. "That night we fell in love," she says. At the end of the year, she releases her debut album, Sweet Kisses, which sells 3.5 million copies. Simpson becomes a cleaner alternative to Britney Spears's suggestive dance numbers by offering innocent contemporary songs like "I Wanna Love You Forever" and "Where You Are."

2001

April

Off and On

Wanting to devote more time to her career and develop a sense of freedom, Simpson breaks up with Lachey. "I couldn't become who I wanted to become," she tells Teen People. "I couldn't be independent while depending on him." The couple reconcile on September 11, the day of the terrorist attacks on the U.S.

Jessica Simpson

May 29

Windless Sales

Showing her bare midriff on the album cover, the preacher's daughter releases her second album, Irresistible, which positions her as more of a bubblegum-pop singer. While the album goes gold, its 500,000 sales are disappointing.

2002

Jessica Simpson

February

Will You Maui Me?

In Hawaii for the NFL Pro Bowl, Lachey charters a catamaran sailboat, setting out with Simpson just before sunset, and waits for "the perfect spot right on the horizon" to pull out an engraved ring and propose. "I was wearing a huge sweatshirt that came down to my knees," Simpson recalls to PEOPLE. "If I'd known he was going to propose, I would have at least dressed cute."

Jessica Simpson

October 26

A Beautiful Church Wedding

In front of 350 guests at Riverbend Church in Austin, Texas, Simpson walks down the aisle in a pearl-covered strapless Vera Wang gown as a beaming Lachey waits at the altar. With the help of his bandmates, he sings (and chokes up during) "My Everything," a 98 Degrees song he wrote for Simpson.

2003

Jessica Simpson

August 19

Marriage 101: The Wince-Worthy

Newlyweds premieres on MTV, giving millions of viewers the chance to watch Lachey and Simpson cry, coo, bicker and make up during their first year of marriage. "Is this chicken or fish?" she famously asks Lachey while eating Chicken of the Sea tuna. "I know it's tuna. But it says 'chicken!'"

2004

Jessica Simpson

January 02

Presidential Seal of Approval

Simpson performs hits off her new album In This Skin for fellow Texan George W. Bush's at the annual Ford Theater gala. She also sang at his inauguration ceremony and pre-inauguration concert for America's Youth in 2001, tailoring her song lyrics "I think that I'm in love with you" to "George, I think that I'm in love with you."

Jessica Simpson

December 01

Preaching About Jessica

In a candid interview with GQ, Simpson's dad Joe says, "Jessica never tries to be sexy. She just is sexy. If you put her in a T-shirt or you put her in a bustier, she's sexy in both. She's got double D's! You can't cover those suckers up!"

2005

Jessica Simpson

August 05

She Wears Short Shorts

The Dukes of Hazzard hits theaters with Simpson starring as Daisy Duke. Before filming, Simpson worked out two hours a day for two months. "I didn't have a butt, so I did lots of squats," she says to PEOPLE.

Photo Credits

BIOGRAPHY (top to bottom): Everett; Steve Granitz/WireImage; Tammie Arroyo; Joe Buissink/WireImage; NEAL PRESTON; amazon.com; Lisa Rose/JPI; Jamie McCarthy/WireImage; WARNER BROS./ZUMA

Edited by Julia Wang

Jessica Simpson

Celebrity Central / Top 25 Celebs

 

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