If you want my Autobiography, Ask Ashlee Simpson
Why Ashlee Simpson's 'Autobiography' Still Resonates 20 Years Later
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I really wish I could pick what pop culture lives in my head rent-free. If I could, I’d have some esoteric-sounding references at the ready, so when someone caught me staring into the middle-distance on Zoom, I could cover and say “oh, I’m so sorry. I was contemplating ‘Rhapsody in Blue’ and it’s melancholy commentary on capitalism.” In this fictional scenario and in plenty of real ones, I am actually replaying the lyrics to things like “Autobiography” by Ashlee Simpson. Today, I need to revisit the importance of this song and album on its 20th anniversary.
I can’t fully explain why that song has stayed with me (besides the fact that it’s incredible). Partly, it may be because Ashlee is not afraid to go there (wish she’d been afraid to go to Ryan Cabrera, but we all can’t get what we want in life).
If you are of my vintage, I want you to close your eyes and remember the opening riff of “Autobiography.” Over a basic beat, she hints she may not be so basic after all and hits us with a provocation:
You think you know me
Word on the street is that you do
You want my history
What others tell you won't be true
Me? *looks in both directions* Is she speaking to ME? This had me clutching my imaginary pearls when I first heard it as a senior in high school in 2004. I did think I knew her. I’d seen Newlyweds, and like any true middle child, was primed to sympathize with a child who has to follow in the wake of an older child. I was also an ardent fan of The Ashlee Simpson Show (RIP) which documented the making of her first album (my previous comments about Ryan Cabrera notwithstanding).
Before her show and album, I’d known Ashlee through her famous sister. So much of her persona seemed to be defined against Jessica. Unlike her elder sister, who seemed like the earnest girl I’d borrow a pencil from in homeroom and then hide from at youth group because she wanted to talk about promise rings, Ashlee seemed rye. She wore eyeliner, and lots of it. I still don’t know how to do that, but found the initiative impressive. She seemed to have a cynicism I felt sometimes (despite earnestness that would make me friends with Jessica). I’m convinced she’s seen at least one episode of My So-Called Life. She probably had a period when she related too much to Holden Caulfield (beige flag). She was relatable. She felt like a person who’d seen the inside of a Hot Topic and Kohl’s. Her hair was blonde, but she let her roots get dark (in fairness, she did warn us: “Sometimes I get dark). She even went full brunette to truly set herself apart (more on this later).
She made an album that in many ways forecasted the rock of Demi Lovato, Miley Cyrus, and other stars trying to break out of the squeaky-clean expectations of their parents’ house without burning it down on the way out. In other words, she was “rebellious,” but not in a way that would ever disappoint her mom. With lyrics like “I walked a thousand miles while everyone was asleep / Nobody's really seen my million subtleties,” she became my teenaged Emily Dickinson. Who amongst us wouldn’t like to believe we’re deep and interesting in ways no one can possibly comprehend?
Ashlee Nicole Simpson began her career as her sister’s background dancer (she’d previously studied ballet). She then took a supporting role on 7th Heaven (red flag) and spent time as a VJ on TRL. This woman lived. Her resume could be the source of millennial celebrity bingo: dated a musician, guest- starred on a family-friendly show, worked on MTV in a now-defunct profession, and dropped a single on Radio Disney.
After her sister’s MTV-reality show, Newlyweds (2003-2005) became a hit, Ashlee got her own show in 2004 to document the making of her first album. To perhaps signal her seriousness of purpose, she dyed her hair brown. As all brunettes know, it’s not that easy to capture what sets us apart. The Ashlee Simpson Show was genius because it brought us in on her journey to “make it” as a musician. Once we saw her process (dying her hair, making out with Ryan Cabrera in his “On the Way Down” music video) we became invested in her success as a little sister with a dream. Sure, we weren’t married to Nick Lachey (red flag), but Ashlee (and us by extension) still had things to say. With songs like “Pieces of Me,” “Shadow,” and “La La,” she put together a legitimately good pop album (despite her claiming to not even listen to pop, a claim her Wikipedia page maintains to this day).
This was 2004, and Ashlee was truly an early example of a Disney-related star trying to launch into adult artistry (She’d had an early Radio Disney single on the Freaky Friday soundtrack. Perhaps a more early 2000s sentence has never been written). She was leaning deep into pop-rock, and though she’d had highs and lows in life, her music had the kind of non-specific lyrical emo quality that made it easy to latch onto and interpret to be about possibly anything. This might be her Autobiography, but that didn’t necessarily mean it was specific to her (which may have been the point).
Perhaps the most relatable aspect of the album was its vulnerability and attempts to articulate frustration as a woman. This was not your youth group purity-ring enthusiast’s album! There are no “With You”- style love songs (I still love that song) or John Mellencamp-appropriated singles (like that one less). Instead, we get this:
Got stains on my t-shirt and I'm the biggest flirt
Right now I'm solo, but that will be changing eventually (Oh)
I laugh more than I cry
You piss me off, good-bye (Good-bye)
Got bruises on my heart and sometimes I get dark
Stains on my t-shirt? Is Ashlee looking at me right now? This week I ate corn on the cob while seated on my couch and left so many kernels behind I’m genuinely considering registering my couch as an energy subsidy. I love that Ashlee writes about being single without embarrassment. I also love the way she claims a rollercoaster of laugh/cry/get dark emotions which somehow felt even then like a preferable alternative to the “live, laugh, love” ethos that her sister projected in songs where she sings she never feels more beautiful than when she’s presumably with Nick Lachey (truly the reddest flag). She may not have had the depth of Kathleen Hannah or Janet Jackson, and Courtney Love would have shoved her in a locker (or worse), but she had something.
There was a time when we were one nation under this bridge:
I'm a badass girl in this messed-up world
I'm a sexy girl in this crazy world
I'm a simple girl in a complex world
A nasty girl, you wanna get with me?
You wanna mess with me?
This nasty girl walked so Tinashe could run. Taylor Swift had this on her mood board during Reputation. Some of us were embarrassed by it then, even as we knew every word! Some of us felt too seen by the earnest attempt at playing a bad girl whose greatest crime was asking for too many samples at SweetFrog. The suburbs yawned at us, and we yawned back. But this song, and its singer, gave us something to scream inside our used Saturns, treading water until we could handle the emotional currents of Joni Mitchell, or god help us all, Stevie Nicks.
I love that the song ends with “If you want my autobiography / baby, ask me.” It’s giving “Come See About Me” by the Supremes (one of my fave songs). Unlike that girl group classic, in which Ashlee’s future mother-in-law sings about the changes she’s made (giving up friends, etc.) to lure her future boyfriend, Ashlee is suggesting you should be chasing her. You think you’re getting her story for free? Try again. She isn’t giving up anything to impress someone, or putting on a front of perfection like the current Bama Rush tiktok girls. Instead, she is showing up messy, perhaps even unapologetically simple. If you can deal with that, and appreciate the “pieces” of her, great. If not, you will end up like Ryan Cabrera, a hat in search of a man.
I don’t want to sully her image by discussing the SNL debacle. I think it was overhyped at the time, and sadly she was just the one person caught boosting her performance with tape when a lot of people do it to this day. In the hindsight of history, should we be mad at her for attempting karaoke with herself? I object only because I find Karaoke upsetting. It always feels like a kid’s talent show but for adults, or a showcase for a room full of people who cannot offer the singer a record deal of any kind, and I can’t emotionally/spiritually handle that. However, even running off stage at SNL, she did something more interesting and memorable than 90% of what happens on that show.
Maybe this song and its album lives in my head rent-free because I too relate to being a messy basic woman who wants their life to feel bigger or deeper than it is. I can imagine Ashlee in a meeting with a label, trying to get signed in the early 2000s. Someone from the label wants to ask how she’s different from Jessica, and Ashlee scrambles to not cite her work on 7th Heaven or as a VJ. It must have been hard to grow up in her shadow, and to want to make some kind of art to find meaning in that. The family defined itself in many ways as a support mechanism for Jessica’s career, which paid off for her.
Ashlee had her brief moment in the sun (mostly 2004-2005), and since then has been digging into her life as wife and mother (and attempted a reality show comeback with her husband that was mostly about wearing pajamas and visiting Diana Ross in Greenwich). I want her to have a musical comeback, and by all accounts, she’s mounting one. Comebacks run in her family. Jessica was able to return to the spotlight and hold her head high after overcoming the tyranny of John Mayer, reinventing herself as a shoe heiress and genuinely talented memoir writer.
Jessica articulated her story so well in 2020’s Open Book in part because she was so candid about the costs of fame and the lessons she learned from weathering relationships with immature men. Far from being an unknowable star or paragon of virtues no one could possibly maintain, she let people see her humanity and people liked her the better for it. When she made her comeback, some seemed surprised at her aplomb, but I think they continue to underestimate her at their peril. Then again, maybe Jessica got that instinct to bare her messy self from Ashlee’s Autobiography. Not sure? Just ask me.
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This is a free post for subscribers of Landline. Consider subscribing to the paid plan to get my weekly email of recommendations and links, a podcast episode, and more! You can also help me spread the word by sharing it with a friend who would love it. Thank you for being a friend!