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* {{Anvilicious}}: '''Quite''' a few episodes, but it ''is'' from the Disney Channel so it's expected. Although a known episode that forced the message hard was "EZ Jackster" which was an obvious attempt to enforce DigitalPiracyIsEvil, reaching {{Narm}} levels considering it's attempts to compare it to ''Film/TheMatrix'' of all things.
* AlternateCharacterInterpretation: Quite a bit:
** Suga Momma's obvious [[TheUnfavorite treatment of Oscar]] has been interpreted as her thinking she screwed up with the other one and is riding Oscar harder so he becomes more successful. Considering that Oscar has a business, a family and grandkids with a wife that loves him compared to her other son, this could hold water.
** Zoey has been interpreted as a ShrinkingViolet who is one of the few people who is Penny's legit friends, and fears Dijonay and Lacieniga more than Penny.
** The Gross Sisters were seen by some as [[StepfordSmiler hiding their true feelings]] and regularly beat people up because they're frustrated at how bad their home life is and how everyone else hates them. [[SelfFulfillingProphecy Which is actually pretty typical of some bullies]]. "Culture Shock" confirms this.
* SugarWiki/AwesomeMusic: The show's soundtrack.
* DarknessInducedAudienceApathy: From Penny's so-called [[WithFriendsLikeThese "friends"]] backstabbing her to the poor treatment on Oscar. Only a limited number of characters are remotely likable, and even then, they have the occasional JerkassBall that makes them just as bad as the others.
* EsotericHappyEnding: "The Legend of Johnny Lovely". An actual boy named Johnny Lovely is suspended from school after dancing with Penny. She then leads a wild goose chase in search of him that ends at the intersection of Johnny Avenue and Lovely Lane. Penny then concludes that Johnny is just a legend and that he may be out there somewhere.
%%* FamilyUnfriendlyAesop:
%%** One episode featured Penny's mother advising her to try and "find some common ground" to resolve a conflict with The Gross Sisters, who had a grudge for her reporting their lunch money extortion to school officials. Said common ground ended up being...[[BrokenAesop offering financial management advice for their stolen money]]
%%** The ''Series/AmericanIdol'' spoof comes to mind, too.
* FunnyAneurysmMoment: In a 2003 episode, Penny is watching a football game and says that Michael Vick is the man. Not so much now, after his dogfighting case lost him the approval of the public.
%%** The episode with Kobe Bryant also became a tad uncomfortable to watch after his highly publicized court case.
* HilariousInHindsight:
** When Oscar listed "the ''Series/SisterSister'' Sisters"[[note]]Tia and Tamera Mowry[[/note]] as some of the most famous twins he knows, the reference sounded dated when the episode first aired, two years after ''Sister, Sister'' ended. Starting the following year, the reference sounded relevant again, when Disney Channel started airing ''Sister, Sister'' reruns.[[note]]Tia and Tamera starring in the ''Literature/{{Twitches}}'' [=DCOMs=] might have also helped.[[/note]]
** Penny mentions WesternAnimation/KimPossible in "The Ballad of Johnny Lovely", but in a manner that makes it unclear whether this show's continuity has Kim as an in-universe celebrity, or just the star of a ShowWithinAShow. After the Proud Family and Kim Possible starred in [[Franchise/DisneyChannelAnimatedUniverse two separate crossovers]] with ''WesternAnimation/LiloAndStitchTheSeries'', the former now seems more likely.
** When Music/{{Beyonce}} had [[UntoUsASonAndDaughterAreBorn her twins]] with Music/JayZ in 2017, a lot of people [[https://78.media.tumblr.com/b4b127af7a193d402ae54695f91158c9/tumblr_oruxjy8kfs1ql5w9mo1_1280.jpg compared]] [[https://78.media.tumblr.com/4b6b68df4313c728f984d3ce05cdd5de/tumblr_oruxjy8kfs1ql5w9mo2_1280.jpg their family]] with the Prouds: Beyonce=Trudy, Jay=Oscar, their older daughter Blue=Penny, and the aforementioned twins=Bebe and Cece. It helps that Bey herself co-performed the theme as part of Music/DestinysChild.
* HoYay: In "The Adventures In Bebe sitting" Dijonay asks if Penny "loves" her, and Penny confirms this. A moment later she calls Dijonay "her girl."
* {{Jerkass Woobie}}:
** Dijonay in the episode "Surf and Turf" when Sticky refuses to kiss her in front of a lot of people.
** Suga Mama in a few episodes, when regards to episodes seeing her much more softer side, such as the episode where she falls in love with a man who Oscar believes is going to cheat on her, but is actually [[spoiler: suffering from Alzheimer's]].
** Oscar. While he can be a jerk sometimes, he suffers the most abuse out of all the characters. He is constantly made fun of by his arch Rival Wizard Kelly for missing the shot at the basketball. He puts up with a lot of stuff and not a single person bats an eye or cares when something bad happens to him or he gets hurt. His own wife treats him like dirt and his Mother shows nothing but abuse and contempt to him. Even cheering against him when he was a basketball star as a teen and hoping he loses.
* TheScrappy:
** Dijonay and Lacienega are this, due to how they treat Penny. Although Lacienega became a LovableAlphaBitch, she still slips back to being a {{jerkass}} and constantly bullies and belittles Penny and other characters. Ironically, the TV movie has Penny continually refer to Zoey as her best friend...guess she dumped Dijonay and Lacienega during the TimeSkip.
** Wizard Kelly counts as well for his callousness and jerkass attitude. He also gains pleasure from bullying Oscar for his failure to win the basketball game he played against him.
* ToughActToFollow: The studio's follow-up to ''The Proud Family'' was ''WesternAnimation/DaBoomCrew'', which was met with an acidic response.
* UncannyValley: Penny in the original pilot. Her head was similar to Stewie Griffin's.
* ViewerGenderConfusion: Some viewers mistook [=BeBe=] for a girl up until the episode where he and [=CeCe=] were turned into teens.
* WheelchairWoobie: Subverted. Penny dates a boy in a wheelchair (voiced by Creator/ShiaLaBeouf) because he made her feel bad for him, only for her to realize he's a {{Jerkass}} who exploits his handicap to get what he wants. Not to mention, the DoubleStandard - Penny and her friends are suspended because they were (wrongly) suspected of having been behind the vandalism. When the true vandal is caught and is revealed to be in a wheelchair, all he has to do is apologize. Naturally, this is ''heavily'' lampshaded and called out on.
* TheWoobie:
** Penny. She usually suffers bad luck from either her friends or her family.
** Zoey, on the episode "Penny Potter" when she feels that nobody notices her.