Contractual Purity: 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.
Crowning Moment of Funny: 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?)
Germans Love David Hasselhoff: 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...
Harsher in Hindsight: "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.
Tear Jerker: Someone's Watching Over Me, Raise Your Voice is one long tear jerker.
Who's That Girl?, Jericho...
Tom Hanks Syndrome: 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.
Unfortunate Implications: She has dealt with some criticism for her "Gypsy Woman" metaphor in that song.