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- OverviewSep 11, 1999-Jan 22, 20008 episodesEpisodes8. The Spanish Imposition; Single, Unemployed Mother Jan 22, 2000
- Pepper Ann is distraught when she can't get into Music Appreciation class; Mom quits her job.
- Pepper Ann befriends Effie Shrug; Pepper Ann goes to a sleep-over at Trinket's house.
- 6. A Kosher Christmas Dec 18, 1999
- Pepper Ann feels she is forced to choose between Hanukkah and Christmas.
- 5. The First Date Club; Unicycle of Life Nov 13, 1999
- Pepper Ann asks Craig to grab some pizza with her, Nicky and Stuart.
- 4. The Wash-Out; Def Comedy Mom Nov 6, 1999
- Pepper Ann accidentally starts a rumor about Gwen having lice.
- 3. Beyond Good and Evel; One of the Guys Sep 25, 1999
- A quest to have a statue of Evel Knievel erected in Lupkin Park; Pepper Ann joins the football team.
- 2. Dances With Ignorance; Girl Power Sep 18, 1999
- Pepper Ann discovers she's part American Indian; Moose's comic book hero is going to be a cartoon.
- 1. You Oughta Be in Musicals Sep 11, 1999
- Pepper Ann auditions for the fast-paced musical romp "Detention!"