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Music / Ashlee Simpson

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"Yes, I can put my head up and I can continue."

Got bruises on my heart, and sometimes I get dark

Ashlee Simpson Ross (previously Ashlee Nicole Simpson and, during her first marriage, Simpson-Wentz), born October 3, 1984 in Waco Texas, is an actress and singer (2001–present) and also younger sister to Jessica Simpson. Early in her career, she scored hits with the songs "Pieces Of Me" and "Boyfriend".

To much of the world, however, she is known for the infamous Saturday Night Live performance in October 2004 where she was caught lip-synching in front of millions of people at home and then proceeded to do a hoe-down for some bizarre reason, followed by a disastrous off-key performance at the 2005 Orange Bowl in which she was booed off stage. She is also an actress, with her best-known role being Violet Foster in the Melrose Place remake. She was married to Fall Out Boy's Pete Wentz and has a son named Bronx Mowgli. Currently married to Evan Ross, the son of Diana Ross with whom she has two children with, a daughter named Jagger Snow and a son named Ziggy Blu.

A cover of her song "La La" would later be included in the cult classic video game Elite Beat Agents.


  • Autobiograpy (2004)
  • I Am Me (2005)
  • Bittersweet World (2008)
  • Ashlee + Evan (2018)note 

Selected Filmography

  • 7th Heaven – Cecilia Smith (2002–2004)
  • The Ashlee Simpson Show (2004–2005)
  • Melrose Place – Violet Foster (2009–2010)
  • Pawn Shop Chronicles – Theresa (2013)
  • Undiscovered – Cela (2005)


  • Chicago – Roxie Hart – 2006, 2009, 2013.

Tropes associated with this singer include:

  • Aloof Younger Sister: Compared to Jessica.
  • All Girls Want Bad Boys: Played straight in "Rule Breaker".
  • Be Yourself: "Love Me for Me", 'Nothing New", "Autobiography", "What I've Become", "Catch Me As I Fall" and "Say Goodbye" as a few examples.
  • Bowdlerization: Façade in "Bittersweet World" is covered up for some reason. "Motherfucking" receiving a Sound-Effect Bleep on "Rule Breaker" is at least understandable.
  • Break Up Song: "Love Makes the World Go Round", "Rag Doll", "Undiscovered", I Am Me, No Time For Tears, Say Goodbye,'' and "Little Miss Obsessive"
  • Darker and Edgier: She's marketed as the slightly edgier alternative to Jessica Simpson's bubblegum pop.
  • Genre Roulette: Bittersweet World runs the gauntlet of Rap, RNB, Dance and duet based pop rock.
  • Fading into the Next Song: 'What I've Become"-"Hot Stuff" on Bittersweet World.
  • From Bad to Worse: The SNL snafu would've been career-crippling in itself, but three months later, she performed at the halftime show for the 2005 Orange Bowl. She had problems hearing the audio during the performance of "La La", causing her to go wildly off-pitch and out of sync with the music, prompting the crowd of 70,000+ to boo her mercilessly. You can see the end of the Orange Bowl performance and the fan displeasure here.
  • Hidden Depths: Although her level of talent has been questioned, she remains to this day the youngest student accepted to the American Ballet Company. She was accepted before Jessica hit it big, as well.
  • Hide Your Lesbians: It is rumored that her character in Undiscovered was originally supposed to be a lesbian before her father stepped in and demanded it changed.
  • Intercourse with You: 'La La", "Kicking and Screaming", "Burning Up", "Coming Back For More."
  • New Sound Album: Bittersweet World used some R&B samples and laid back grooves.
  • Oh, Crap!: Her reaction to the wrong song playing during her Saturday Night Live performance, leading to her hoe-down dance.
  • Screw This, I'm Outta Here: Walked off the set of Saturday Night Live when she was caught lip-synching.
  • Shotgun Wedding: Formerly to Pete Wentz of Fall Out Boy.
  • Silly Love Songs: 'In Another Life", "Never Dream Alone", "Endless Summer", 'Pieces Of Me'
  • Stage Mom: Gender-flipped. Her dad was, shared with Jessica Simpson.
  • Take That!: "Bittersweet World", the song towards Hollywood... and "What I've Become" to people who dislike her evolution over time.
    • Shadow to her parents to side lining her in favour of Jessica.
  • That Syncing Feeling: Infamously, her appearance on Saturday Night Live was ruined when her vocal track was cued too early, revealing her to be lip-syncing. She panicked and improvised a hoe-down dance before running offstage.
  • Tsundere: The idea behind her debut album, especially songs like "Love Me For Me", "Autobiography" and "Surrender", but it's always an element of her music.
  • The Lad-ette: "Rule Breaker" and "Autobiography" indicate this. Also how she was invented as the Anti–Jessica Simpson.
  • Rock Star Song: "Bittersweet World", essentially.
  • Tomboy: Compared to her sister.
  • Vocal Evolution: She gets less husky and more strong and secure in her vocals from her debut to third album.

You want my auto, want my autobiography, baby just ask me


Video Example(s):


Ashlee Simpson lipsyncing

"Pieces of Me" starts when Ashlee Simpson is still standing with the microphone at her hip, and she gives an embarrassed "hoedown" and walks off stage.

How well does it match the trope?

5 (16 votes)

Example of:

Main / ThatSyncingFeeling

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