History YMMV / AshleeSimpson

* CondemnedByHistory: As a pop star, at least. In the early 2000's she was one of the most popular singers on the market, with her debut album ''Autobiography'' going triple platinum. Then along came her disastrous ''SNL'' performance, followed shortly thereafter by another even more disastrous performance at the Orange Bowl. Together, these two incidents created the impression that Ashlee couldn't actually sing without studio help. While her second album was a #1 album, it sold well below her first and then plummeted the next week afterwards, and the third album barely made a dent in the public consciousness, signaling her music career was all but over. While she's had a bit more success as an actress, whenever she's brought up today, it's usually in the same breath as Music/MilliVanilli, as the punchline of jokes about lip-syncing and manufactured pop stars.

* NeverLiveItDown: Her disastrous SNL and Orange Bowl performances. For the first, she was caught lip-synching and she tried covering it by doing a jig before leaving the stage. This likely had an impact on the second, where she was booed before her performance even ended.

* SugarWiki/AwesomeMusic: Depending on where you're coming from, young angsty/{{wangst}}y pop-rock-loving-teenagers can love ''Autobiography'', people who suffered recent letdowns can love ''I Am Me'' and people who love a mishmash of sounds and BeYourself theme can love ''Bittersweet World''.

** Go on YouTube and watch the video of her Orange Bowl performance. At 0:22 you can actually hear someone yell out “YOU SUCK!” Also, the camera cuts away from her before showing her reaction to the booing.

* DeaderThanDisco: As a pop star, at least. In the early 2000's she was one of the most popular singers on the market, with her debut album ''Autobiography'' going triple platinum. Then along came her disastrous ''SNL'' performance, followed shortly thereafter by another even more disastrous performance at the Orange Bowl. Together, these two incidents created the impression that Ashlee couldn't actually sing without studio help. While her second album was a #1 album, it sold well below her first and then plummeted the next week afterwards, and the third album barely made a dent in the public consciousness, signaling her music career was all but over. While she's had a bit more success as an actress, whenever she's brought up today, it's usually in the same breath as Music/MilliVanilli, as the punchline of jokes about lip-syncing and manufactured pop stars.

* UnnecessaryMakeover: Why oh why did she have to get a nose job? Now she's just another person.

* WhoNamesTheirKidDude: [[BigApplesauce Bronx]] [[Literature/TheJungleBook Mowgli.]] ''Really?''

* EarWorm: You couldn't get "La La" out of your head, could you? It's even a song on ''VideoGame/EliteBeatAgents''.
** Even better is "L.O.V.E." L.O., L.O., L.O., L.O.V.E., L.O., L.O., L.O., I'M TALKIN' BOUT LOVE!!!!

* GrowingTheBeard: Her voice is more empowered and stronger in ''Bittersweet World''. The performances improved as well during that time, as her vocal quality and stage presence grew exponentially, no doubt due to her Broadway run as Roxie on ''Theatre/Chicago''.