1. Her logo was basically the cover of a Lisa Frank Trapper Keeper.
Look at that font!!! So Clarissa Explains It All.
Even when she became edgier and dyed her hair black-brown. The logo is still the stuff of tween dreams.
2. She never took anyone’s crap.
Independent lady by 19, vocal virtuoso by 20… all caught on camera! Thanks, MTV.
3. She made sure we all knew how to L.O.L.O.LO.L.O.V.E.
May this jam stay forever in our hearts.
It’s in her songs and it’s on her show. What could be better?
5. She was very vocal about her active romantic life.
Which was awesome for us because she’s so darling and head over heels, like, 100% of the time.
6. First, this was the cutest couple ever…
His name is Josh Henderson, he’s an actor/model/all around renaissance man. Unfortunately their relationship doesn’t survive past episode three.
7. …then this…
I personally like to believe every Ryan Cabrera song was written about Ashlee.
8. …until this was the cutest couple of all time.
Why is this still not a thing? Ughhhh.
9. There was an entire episode dedicated to SNL damage control.
After lip-syncing on Saturday Night Live, Ashlee Simpson responded by doing a hoedown jig—not the most graceful move. Following the mishap, Simpson called into MTV’s TRL and blamed the situation on severe acid reflux. We feel ya, girl!
10. She spent her 20th birthday at Medieval Times.
Because she is a delightful human being. Also: her band presented her with “adult” gifts. How could you not want to watch that?
11. She hosted taco parties with her friends.
Just like you and me!
12. There was that one time Ryan Cabrera told Ashlee: “You know what I love about you? You have the eyes of a gorilla.”
“Don’t gorillas have green eyes?”
No, Ryan. Gorillas do not have green eyes.
- At least 86 people were killed in twin bomb blasts during a peace rally near the main train station in Turkey's capital. ›
- Activists are celebrating the 20th anniversary of the Million Man March at the National Mall in Washington, D.C. ›
- Elections on Sunday are widely expected to hand Belarusian President Alexander Lukashenko a fifth term since 1994. ›