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21 Episodes 2001 - 2002
Episode 1
Sat, Sep 15, 200122 mins
When a rich new family moves in next door to the Prouds, the parents hit it off right away, but Penny can't get along with their luxurious but vain daughter LaCienega, who tries out for cheerleading with Penny. When Penny makes a remark the she wants LaCienega out of her life, local bullies the Gross Sisters take it upon themselves to grant Penny's wish. After her friend Sticky brings word of the Gross Sisters' plan, Penny must decide between wanting the glory for herself or allowing her new rival a fair chance.

Episode 2
Fri, Sep 21, 200121 mins
Penny is upset by the small allowance her parents give her for doing chores. Penny and her friends want to do something fun together, but they realize that everything is too expensive for their small allowances. Penny and her friends then go on a strike against their parents to demand a raise in their allowance. Until their demand is met, the children live outside, where they protest with signs while consuming bugs for nutrition. The children's strike is eventually broadcast on television news, but Oscar still declines to raise Penny's allowance. Eventually, Penny's friends abandon the strike when they realize how difficult it is to be away from the comfort of their houses. Penny, the last remaining striker, ultimately reaches an agreement with Oscar for a raise in her allowance.

Episode 3
Fri, Sep 21, 200122 mins
When Penny persuades her parents to have a sleepover, things get a little out of control when Dijonay brings a bunch of other kids to the newly proclaimed "party". Penny and Myron get locked in a closet, where Penny realizes Myron is claustrophobic. At school, everyone is talking about a rumor that Penny and Myron are a couple.

Episode 4
Fri, Sep 28, 200122 mins
Penny is bored sick of her mother's veterinary job on "Go To Work With Your Mother Day", until a magician with a very despondent tiger shows up at the clinic. Penny forms a bond with the tiger, but her mother, Trudy becomes wary. Oscar tries to go to a basketball game, but the only way he can go is if he sells ice cream at the game, which attracts women, including Wizard Kelly's gorgeous wife, Ginger S. Kelly.

Episode 5
Fri, Oct 5, 200121 mins
Penny is used as a tool to infect the whole world with a website marketing illegal free music downloads using the philosophy that "free music is our birthright." This episode is based on The Matrix. Guest Star: Ray J as Mega. Note: The episode name is a reference to Napster.
Episode 6
Fri, Oct 12, 200122 mins
When Wizard Kelly launches a spelling bee competition, Oscar forces Penny to train and makes her enter the competition so that he can re-live his glory days all over again, but the son of a contestant who lost to Oscar in a spelling bee that happened years ago made other ways to win the competition. Guest Stars: James Avery as Crandall Smythe, Ken Lawson as Timothy Smythe, and Ron Glass as the Talking Baby.

Episode 7
Fri, Oct 19, 200122 mins
When Penny tries to impress a boy she likes at school, she ends up on the football team, but Coach Collins refuses to let her play since she is a girl. Penny is finally given her chance when Michael, the coach's son, refuses to play out of fear. Penny then proves herself a capable football player, earning the respect of her teammates. Meanwhile, Oscar develops a new food for the Proud Snax brand called jelly poppers, which pop in more ways than one. Guest Star: Mablean Ephriam as the Judge.

Episode 8
Fri, Nov 2, 200122 mins
Breaking her father's strict "no-dating rule", Penny goes with her friends to the amusement park. Thanks to LaCienega, she ends up with an un-popular, overweight boy named Carlos. Penny thought that Carlos would be a nerd, but ended up being a very caring person and saves Bebe and Cece's lives when they sneak on a roller coaster after they escape from the baby care center at the park. Guest Star: Kel Mitchell as Carlos.

Episode 9
Fri, Nov 9, 200122 mins
Penny's grades fall victim to a longtime grudge held between her teacher Ms. Dinkins and Suga Mama. Oscar and Trudy decide enroll the twins in a private pre-school, but change their minds at the last minute. Thanks to Penny in the end, Suga Mama and Ms. Dinkins became friends again and Ms. Dinkins does the right thing and changes the grade on Penny's paper from a "D" to the one she deserves: an "A". Guest Stars: Dorien Wilson as Dave Daniels and Hattie Winston as Gertie Dinkins.

Episode 10
Fri, Nov 16, 2001
Penny is given a credit card, leaving her to spend massively without her parents knowledge. She then learns the value of a dollar and how credit cards really work. Meanwhile, Oscar tries to get rid of a mouse in the Proud's home, but the Prouds' annoying, 9 year old neighbor Peabo creates more problems for Oscar. Guest Star: Steve Harvey as the Credit Card. Note(s): The song Independent Women by Destiny's Child is featured; this is the only episode not on Disney+, in fact, this episode cannot be streamed anywhere.

Episode 11
Fri, Dec 7, 200122 mins
The Proud Family is taught an important lesson about the true meaning of Christmas and Kwanzaa by a homeless family. Guest Stars: Vivica A. Fox as Margaret, Samuel L. Jackson as Joseph, Raven-Symoné as Stephanie, and Pat Crawford Brown as Agnus.

Episode 12
Fri, Dec 14, 200122 mins
Penny, LaCienega, and Dijonay give Zoey a makeover for the school dance. When Nubia Gross sees Zoey's makeover, she forces the girls to give her younger sister, Olay one too.

Episode 13
Fri, Jan 4, 200222 mins
Oscar and Trudy allow Penny to have a house party for her friends, but Penny finds out that her friends would rather go to LaCienega's party that is on the same day. When Penny's party is a bust because no one shows up, the Proud's and a few surprising people team up to show her that it's not the quantity of your guests, but the quality that makes a great party.

Episode 14
Fri, Jan 18, 200222 mins
At a barbecue, Oscar nearly burns the Boulevardez's house down, and the Prouds take their neighbors in while they await repairs, much to the chagrin of Penny who is forced to share her bedroom with LaCienega. But when an embarrassing Boulevardez family trait is revealed during swimming class, Penny finds that the idea of her rival being knocked down off her high horse isn't as enjoyable as she thought it would be.

Episode 15
Fri, Feb 1, 200222 mins
For Black History Month, Penny and her friends are given school assignments to dress up as prominent black people and give a presentation on how each person contributed to black history. At school, Penny slips on a wet floor that was just mopped. Later, at her house, Penny is tasked with dropping Puff off at a groomer on her way to school, where she will give her presentation on Angela Davis. Penny and Puff get caught in a wind storm on the way to school. Afterwards, Penny is confused when she learns that her friends no longer spend time with Zoey because she is white. When Penny returns home, she learns that the year is 1955. Despite their differences in skin color, Penny becomes friends with Zoey, going against what is considered normal. Penny and Zoey convince their class to unite against segregation, and Penny eventually convinces an outraged mob of the same concept after reciting Martin Luther King Jr.'s "I Have A Dream" speech. Penny wakes up and learns that she was only dreaming, having gone unconscious after falling on the wet floor at school. Guest Stars: Thomas Mikal Ford as Mr. Webb and Stephen Root as Mr. Andrews.

Episode 16
Fri, Feb 8, 200222 mins
Penny is guilt-tripped into forming a relationship with a boy in a wheelchair on Valentine's Day. However, the boy turns out to be obnoxious and rude, prompting Penny to break up with him. Guest Star: Shia LaBeouf as Johnny McBride

Episode 17
Fri, Mar 1, 200222 mins
Oscar is trying to enjoy "Oscar Day", but Suga Mama shows up to drop off Puff while she goes to her Tae Bo class. Trudy then drags Oscar out to shop for new furniture, leaving Penny to watch the twins and Puff. When Penny gets roped into a game with her friends outside, Bebe and CeCe antagonize Puff, causing them to run away. Penny manages to rescue the twins, but Puff ends up falling into the river. Suga Mama is depressed without her beloved poodle, and while the family and friends try to find him, Puff has a series of adventures including nearly being sacrificed into a volcano and appearing on magazine covers in Paris.

Episode 18
Fri, Mar 15, 200222 mins
Penny decides it's time to stand up to the neighborhood bullies, the sisters, who relentlessly shake down the student body for their money. When the Gross sisters hear that it was Penny who snitched them out to the school principal, Penny learns how to lead them with conversation instead of confrontation in order to save her own skin. Also, Oscar and Trudy take the twins to Dr. Payne for their shots.

Episode 19
Fri, Apr 12, 200222 mins
Sticky, in dealing with his parents divorce, starts hanging out with a group of bullies called 'The Altos.' In order to knock some sense into Sticky, Trudy and Penny recruit Oscar to expose Sticky to The Proud Snack Factory believing Sticky will find a positive role model in Oscar. Unbeknownst to the Prouds, Sticky has ulterior motives and steals the clues to a scavenger hunt contest being co-sponsored by Proud Snacks and Wizard Enterprises. Meanwhile, Oscar is gypped by Wizard Enterprises when his company logo is not visible to the naked eye, but when viewed under a magnifying glass, reads 'Prune' instead of 'Proud' Snacks.

Episode 20
Fri, Apr 26, 200222 mins
Penny and her friends form a dance group known as "LPDZ", and dance on "Hip-Hop Helicopter", a famous dance show. Oscar gets furious due to their skimpy outfits. A conversation with Trudy convinces Penny to not wear the outfit anymore, but when Dijoany's cousin invites them to a high school party, Penny and her friends deal with the peer pressure of "acting cool" while lying about their ages. Elsewhere, the Proud and Boulevardez families compete against each other in bowling, and Oscar is obsessed with beating Suga Mama at the game. *Notes*: Hip-Hop Helicopter is a parody of Soul Train. In this episode, we learn that Dijonay's cousin Bethany works for Hip-Hop Helicopter. Guest Stars: Big Boy as himself, Shaun Robinson as herself, Shar Jackson as Bethany, and Lamont Bentley as Gary.

Episode 21
Fri, May 24, 200222 mins
Penny is cast as 'Juliet' in the upcoming school play of Shakespeare's 'Romeo and Juliet.' Penny finds herself having a crush on her fellow cast member Kwok, who is playing 'Romeo,' and is nervous when she finds out there's a kissing scene in the play.
