Jessica Simpson on the cover of Vanity Fair

Do you remember Jessica Simpson? That delightfully-dizzy blonde who ruled MTV in an era long ago and far away? (You know: before Twitter, the Jonas Brothers, Octomom and So You Think the Plus Eight Stars are Rock of Love in The Hills?) There was a time when I was–yes, I think I’m brave enough to admit it now–obsessed with Jessica Simpson. Sure, I poked fun at her. I ruled the Nick and Jessica Breakup Watch (RIP!) with an iron fist. I rolled my eyes in annoyance at her twee observations. But I loved her all the same. Truly. She felt like family–that sister or aunt who frustrates you to no end, but when your boyfriend makes fun of her, you snap.

Improbably, over the past 4 years, Jess has become the underdog. I can’t put my finger on it, but there’s something simultaneously heartbreaking and inspirational to me about Jessica Simpson. I root for her. I wish her well. I feel–in the lamest possibly way–that we will someday be friends. Despite being beautiful and having an air of the Homecoming Queen, she’s at her best when she’s dorky, relatable, stripped bare. Glamorous Jess? No. Jess being propelled through the water and faceplanting into a dolphin’s belly? Mais, oui.

I suspect I’m probably alone in my bizarre Jess-cheerleading. That’s okay. I’m waiting for her Britney-style comeback (make it happen!) and look forward to the day when we’re downing margaritas on my deck together and I say, “So…I have a confession. I used to keep this blog called Nick and Jessica Breakup Watch…”

Stranger things have happened, right?
Tags: Jessica Simpson, Vanity Fair
6 Responses to “Jessica Simpson on the cover of Vanity Fair”
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May 4th, 2009 at 8:31 pm
The strange thing is, despite her misgivings and failures, I’ve been kind of rooting for her too. Which compelled me, the other day, to Netflix the entire “Newlyweds” series, which I watched way back when it aired. It’s kind of like watching a train wreck where you know the outcome, but sort of enjoy the ride.
May 4th, 2009 at 8:38 pm
I will admit that I cheer her on too! She’s a good person, gorgeous, and has a heart of gold from what I see so she’s one that I can’t root against. I really hope that a reinvention of herself comes along and she makes it back in the spotlight in a good way, or at least finds some peace and happiness.
May 4th, 2009 at 9:13 pm
Umm, I have always thought I would be besties with her one day too! And we both went through our divorces at the same time, so I used to feel like we had a bond and that if we met, we would immediately hit it off! The southern thing too, of course.
May 4th, 2009 at 9:37 pm
root away…I love her too! I think she is genuine and lovely!
May 5th, 2009 at 1:37 pm
I know what you mean. She used to annoy me, but now I feel sorry for her. She seems like a nice girl, and I think it’s preposterous how much negative attention has been given to her weight, considering how awesome her body is.
-T
May 5th, 2009 at 2:04 pm
Yeah, I hope she finds her groove again. Not sure about a Britney-style comeback, though. Something still seems off in Britney Land. A lot of people played a hand in that. Luckily it sounds like Jessica has a strong family unit.