In 2004, Ashlee Simpson was primarily known as a little sister. By the time she began working on her debut album, her older sister Jessica Simpson had skyrocketed from a young, Southern, blond pop princess to a bona fide A-lister, thanks to the hit reality show The Newlyweds, which chronicled Jessica’s marriage to 98 Degrees heartthrob Nick Lachey.
As a teen, Ashlee was famous by proxy. She toured with her sister and started to act on TV shows like Malcolm in the Middle and 7th Heaven. Her singing ambitions stayed on the backburner until she hit her twenties — that’s when she got a major break and recorded the spunky Freaky Friday soundtrack cut “Just Let Me Cry,” a sharp, pop-punk contrast to the saccharine bubblegum sound all over her sister’s discography.
It was because of this opportunity that Ashlee got her first record deal. She spent 2003 recording what would become Autobiography, an album that turns 20 this week. (She was simultaneously making her own reality show series The Ashlee Simpson Show, which chronicled the album process and also became a hit). With new jet-black hair and thick black eyeliner, Ashlee set herself apart not only from her sister but from many of the other pop girls that the the industry probably intended for her to compete with at the time. Instead, she fit herself into a post-Avril Lavigne musical landscape with ease, writing confessional guitar-driven cuts.
What worked for Ashlee was leaning into a messier, less pristinely built image than her sister’s had during the early peak of her pop career. Her voice had a distinctly edgy rasp that she yelped out those scream-along lyrics with. On the chorus of title track “Autobiography,” she celebrates her stained t-shirt and the flirty side of recovering from a heartbreak. Meanwhile, power ballad “Shadow” addresses the anxiety of sharing the same ambitions as an already-famous sibling.
It’s the album’s lead single, however, that most perfectly executes Ashlee’s mix of early twenties chaos with her specific brand of karaoke-ready, catchy, rock-tinged cuts. “Pieces of Me” is a love song written about her then-boyfriend Ryan Cabrera, where Ashlee fesses up to her flaws to a person who already loves all of them. It’s adult-contemporary, Vh1 Top 20 Countdown-core with a twist; the song is sensitive and earnest with that hint of rebellion that Ashlee carried so well.
Over the past two decades, Autobiography has held up as well as it did upon its release. It was 2004’s biggest debut album by a female artist and went triple platinum. The singles were international hits, with “Pieces of Me” hitting Number Five on the Billboard Hot 100.
Of course, all of the work Ashlee had done to show she as not only her own artist but a great one at that faced a major setback when she appeared on Saturday Night Live in October of that year, a few months after her album had already taken off. She had lost her voice the day of her appearance and decided to use a pre-recorded track to lip-sync to. When the wrong vocal track accompanied the band’s live performance, Ashlee proceeded to do a “hoedown” dance as the show cut to commercial.
The backlash wave put a wrench in people’s idea of her authenticity, but that didn’t stop Ashlee from releasing a streak of excellent songs over her next several albums. Singles like “Boyfriend” and “Outta My Head” proved she could be as much a pop princess as her sister and peers — but she never had to lose her edge. And for the young listeners who loved Autobiography and Ashlee in spite of the public’s disapproval, the album has continued to remain one of the most prescient and raw releases from that era. And at 20 years old, the same age Ashlee was when she made it, it still sounds as fresh, fun and relatable as it did in 2004.
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