* ContractualPurity: Hilary kept a low profile for years, and she only got minor controversies. However, said attempts to make her image filthy were minimal, and failed to even leave a dent on her good girl image.
* CrowningMomentOfFunny: ''Do You Want Me?'', the song itself is so out there and tongue in cheek and oh so true wherever you were in high school (Life?)
* GermansLoveDavidHasselhoff: In Italy, she's considered ''very'' popular there. Must be why they had their own exclusive Best of called 4ever Hilary Duff in 2006, during her one sort of break...
* HeartwarmingMoments: ''Jericho, Someone's Watching Over Me, Now You Know, Fly''
* HarsherInHindsight: "Daddy's always there" in Sweet Sixteen can be seen as cringe worthy considering her now fractured relationship with her father due to his cheating on her mother.
* HilariousInHindsight: Listen to "So Yesterday" and try not to laugh.
* TearJerker: ''Someone's Watching Over Me'', '''Raise Your Voice''' is one long tear jerker.
** ''Who's That Girl?'', ''Jericho''...
* TomHanksSyndrome: After her Lizzie stint, Hilary was typecast in her typical tween-appealing roles before venturing for slightly more dramatic territory in ''Raise Your Voice'' and ''The Perfect Man'' (the latter somewhat less serious than the former). In both cases, it backfired when the films bombed at the box office and critics slammed not only the films, but also her performance.

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