* 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?)
** When ABCFamily broadcasted ''LizzieMcGuire'' reruns on prime time in December 2014, Hilary live-[[{{Twitter}} tweeted]] [[https://twitter.com/HilaryDuff/status/549814916442357761 this]] post. Also counts as SophisticatedAsHell and, in a way, along with the [[https://twitter.com/HilaryDuff/status/549818691106263040 following tweet]], a {{Heartwarming Moment|s}}.
* EarWorm: An entire textbook of them. "Fly", "So Yesterday", "Come Clean", "Wake Up", "With Love", "Stranger", "Why Not", "Danger", "Beat of My Heart", "Chasing the Sun", "All About You", "Sparks".
* GermansLoveDavidHasselhoff: In Italy, she's considered ''very'' popular there. Must be why they had their own exclusive GreatestHitsAlbum called ''4ever Hilary Duff'' in 2006, during her one sort of break...
* HeartwarmingMoments: "Jericho", "Someone's Watching Over Me", "Now You Know", "Fly".
** Her [[http://www.huffingtonpost.com/2015/05/14/what-lalaine-lizzie-mcguire-has-been-up-to_n_7235820.html 2015 reunion with Lalaine and Jake Thomas]] from ''Series/LizzieMcGuire'', neither having been in touch with Hilary for 14 years.
* 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.
* {{Narm}}: "So Yesterday" has the line "If the light is off, [[CaptainObvious then it isn't on]]." Also, see HilariousInHindsight above.
* TearJerker: "Someone's Watching Over Me", "Who's That Girl?", "Jericho".
** ''Raise Your Voice'' is one long tear-jerker.
** "Love Just Is" gravitates between this and [[HeartwarmingMoments Heartwarming Moment]].

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