The 10 Ashlee Simpson Songs to Help Prepare for Her 2017 Comeback

Ashlee Simpson performs during 11th Annual Music Midtown Festival in Atlanta.
Chris McKay/WireImage

Ashlee Simpson performs during 11th Annual Music Midtown Festival in Atlanta.

While the world already had their eyes on Jessica Simpson at the turn of the century — thanks to a handful of hit singles, a burgeoning acting career and an MTV-captured romance with 98 Degrees’ Nick Lachey —  it wasn’t until 2004 that people got to know Jessica’s little sister Ashlee, thanks to her own MTV series, The Ashlee Simpson Show. The show chronicled Ashlee’s journey recording her first LP Autobiography, and hinted at the differences her music would display from her sister’s: instead of starry-eyed hooks, Ashlee’s songs came with a delicious pop-punk edge.

Ashlee would go on to release two more albums following her 2004 debut, and was slated to release another in 2012, but scrapped it after her single “Bat For a Heart” fizzled. For the past nine years, Simpson has mainly stayed out of the limelight and focused on her family — the mother of two was previously married to Pete Wentz, and now is married to actor Evan Ross — although she recently confirmed plans to release new music in 2017, with Ross as a collaborator.
Is the Ashlee Comeback nigh? Just to be safe, brush up on her underrated discography and listen to the 10 most essential tracks of her career thus far.

“Pieces of Me”

“Pieces of Me” was Ashlee’s introduction to the world as a singer-songwriter, and the first single from her debut LP Autobiography remains a bit self-indulgent, but unbelievably catchy. As Ashlee lilts the chorus (“It's as if you know me better/Than I ever knew myself"), it’s clear that “Pieces of Me” should have been the theme song to Laguna Beach (sorry, Hilary Duff).

“La La”

The grittier the better when it comes to Ashlee’s music — and with “La La,” she doesn’t hold back, saying how she prefers her romance rough ("You can throw me like a lineman/ I like it better when it hurts"). What drew listeners into this track was the Joan Jett-like snarl that joined the guitar riff and raspy vocals.


While not all of Ashlee’s singles were commercially successful, “Boyfriend” might have hit its mark the most effectively. On the first advance track from her sophomore album I Am Me, Ashlee reveals a harder rock side while she sings about not stealing someone else’s BF. Rumors swirled that “Boyfriend” was about Ashlee’s supposed relationship with Wilmer Valderrama, who had been previously dating Lindsay Lohan. While Ashlee maintains the song is a general statement, we still can’t help but wonder.


In some ways, “L.O.V.E” had allusions to Christina Aguilera’s “Dirrty” phase, but it mostly served as a girl-power anthem. Something that makes Ashlee’s music so beloved is how relatable the lyrics are, and Ashlee perfectly captures the relief of setting her guy’s unanswered calls aside and partying with her girls.

“Little Miss Obsessive”

Ashlee’s third album lacked the cohesiveness of her first two albums and generally sounds over-produced, but “Little Miss Obsessive” gloriously returned to her Autobiography days. This deep cut showed the reality of late-night hangs with your ex (“Late night you make me feel like I'm desperate, I'm not desperate/ Oh, a little bit possessive, little miss obsessive, can't get over it”). We heard you, Ashlee, and we sympathized with you.

“I Am Me”

Ashlee wasn’t trying to be her insanely successful big sister, Jessica -- she was forging her own path. On “I Am Me,” we see Ashlee belting about how she refuses to compromise for anyone. Although it slipped through pop radio's cracks, it’s one of Ashlee’s best empowerment anthems.


The title track of her debut album was a dark, guitar-heavy centerpiece: as Ashlee sings, “Got stains on my t-shirt and I'm the biggest flirt/ Right now I'm solo, but that will be changing eventually,” it’s easy to think how this could have been a smash for Avril Lavigne. The lyrics humanize Ashlee, and the song stands as a great soundtrack for angry-cleaning your apartment.


Ashlee left listeners with a raw, vulnerable closer on Autobiography. The “Undiscovered” melody sounds like it could be from an early Nada Surf record, but the vocals are clean, and the guitars shimmer as Simpson longs for the past in a broken present. Stripping away any pretense, “Undiscovered” is perhaps the most sincere song of her career.


On “Surrender,” Ashlee finally channels her inner Courtney Love, giving in to some nifty guitar-shredding and pushing the swagger upfront. As Ashlee sings the chorus, “Oh you drive me crazy, oh you just bring me down/ Look out your window, my sunshine’s all around,” she oscillates between being over someone who’s bad for her and running back to them. Any teenager knows this saga, but Simpson made the story seem fresh.

“Beautifully Broken”

“Beautifully Broken” finds Ashlee rising like a phoenix from the ashes after a much-maligned SNL performance that revealed she used a backing track. The sparse track shows Ashlee owning up to the incident (“I am beautifully broken and I don’t mind if you know it”), and stands as a reminder that Ashlee is just as imperfect as the rest of us.