Jessica Simpson in 2000 and 2014
Wireimage; FilmMagic
Jessica herself has posted this video before, tweeting it as "The ultimate #tbt." In the clip, the then-high schooler plays the role of Cassie in A Chorus Line, absolutely belting out "The Music and the Mirror." The other appropriate hashtag might be #nailedit.
Jessica's first-ever single was "I Wanna Love You Forever," which was released in September 1999. She looks so young but so confident as she sings for a photographer in front of ever-changing, ominous-looking backgrounds: a barren desert, an empty scrub plain, the middle of the ocean. We're not exactly sure what's going on, unless she's Miss January in the "Places You Could Hide a Dead Body" calendar.
What better way to celebrate a birthday than by remembering … another birthday. In 2000, Jessica and her center-parted hair celebrated her 20th at Sony Picture Studios, with a massive cake that had her face airbrushed on the icing. That's a nice gesture, but we would've felt weird asking for a slice of her collarbone.
Jessica Simpson at her 20th birthday party in 2000
SGranitz / WireImage
In 2001, she performed in a concert during the inauguration ceremonies for then-President George W. Bush, closing the evening's show with her own "I Think I'm in Love with You." Only Jessica could've pulled off this outfit, which sort of looks like she's wearing a fur-trimmed leather loveseat.
Jessica Simpson at the 54th Presidential Inaugural in 2001
Mark Wilson / Newsmakers / Getty
Jessica was a guest star during the fifth season of That '70s Show, playing Michael Kelso's girlfriend Annette Berkardt. The role required her to frequently make out with Ashton Kutcher, which is a plot point that might've been written by Ashton Kutcher.
Who can forget Jessica and Nick Lachey? The reality-show Newlyweds couldn't have been more adorable if they'd been designed and sold by Mattel. We're less surprised that we'd forgotten this March 2004 Teen People cover than we are that we'd forgotten that people used to wear cap-sleeved baseball tees.
Jessica Simpson and Nick Lachey on the cover of Teen People in 2004
Even if you didn't watch Newlyweds: Nick and Jessica, you've totally seen this clip from the very first episode – the one where Jessica is unsure whether Chicken of the Sea-brand tuna is chicken or fish. Eleven years later, and we're still disappointed that no one ever asked her to explain Grape-Nuts.
In 2005, Jessica starred in the Dukes of Hazzard remake with Johnny Knoxville and That Guy Who Will Forever Be Known as Stifler. She also did this insanely hot video for "These Boots Are Made For Walking," the one where she and her Daisy Duke cutoffs turned the head of Willie Nelson and every cowboy within a 200-mile radius.
If we turn the Throwback Machine to 2007, we'll see Jessica and her dark hair in a relationship with John Mayer. We still don't fully understand that one. John later referred to her as being "like crack cocaine" to him, a sentiment that might've sounded more romantic in his head.
John Mayer and Jessica Simpson in 2007
Kevin Mazur / WireImage
In 2009, Jessica performed at a Chili Cookoff in Florida and wore a pair of high-waisted "mom jeans" that prompted all kinds of unwanted scrutiny about her weight and her appearance. Five years later, people are STILL talking about those pants. "What's more unbelievable is that the press could create something like that out of a pair of jeans," she told Redbook in January. "What woman wants to be brought down for wearing a pair of jeans?"
Jessica Simpson in 2009
Logan Fazio / Getty
Eric Johnson and Jessica Simpson
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