Sick of the grind of everyday preteen life, Pepper Ann gets involved in a medieval fair, where she pretends she's Lady Gwynne.
A Balladeer tells the tale of Pepper Ann and her alter ego Lady Gwynne of Bottle. Pepper Ann, tired of studying algebra, as well as the numerous chores that Lydia has for her, has to step out to go to the dentist. As Milo and Nicky wait for Pepper Ann to return so that they can study, Crash challenges them and Moose to a game of Anti-Trust, which they obsessively play throughout the entire episode. Pepper Ann humiliates herself in front of Craig after her numbed mouth results in her drooling chillade and then rollerblades home, only to fly off a sign and crash through a roof of a barn. She sees people in medieval attire and believes she has traveled back in time to 1596.
Pepper Ann disguises herself and then encounters a wizard and asks to return her to her time period. The Wizard gives her tassels to run with and she finds herself back in modern times, only to be informed by Constance that she was at the renaissance faire. Embarrassed, she returns home, but quickly begins to miss the festivities. Donning a medieval outfit of her own, she makes plans to return to the faire, despite Lydia and Nicky reminding her that she needs to study for algebra. Pepper Ann quickly takes to the Elizabethan style of speech and becomes popular with the residents, including a young boy named Guiles of Cork whom she quickly befriends.
Pepper Ann starts to love living her life as Lady Gwynne at the faire and begins to lose touch with reality. After getting a C- in algebra and humiliating herself in front of Craig again, Pepper Ann continues to return to the faire to the point that she still speaks Elizabethan to people when she is at home; upsetting Lydia and the school. With no other option left, she tells the people at the faire that she must return home now. Guiles offers to see her again at the Greezy 'n' Cheezy to which she accepts. However, she arrives still as Gwynne and meets Guiles, real name Gary, who offers to help her with her algebra, but she disappointingly turns him down.
Pepper Ann returns to the faire, but is confronted by the Wizard who knows her actual name and the troubles she has been facing. He convinces her that while medieval play is fun, she needs to return to reality where people care about her. Taking his words to heart, she leaves and it is revealed that he is a real wizard. Pepper Ann, as herself, meets back up with Gary and takes up his offer to be tutored at algebra. She takes him home where they end up chasing after Sir Talonsworth, a falcon that Pepper Ann had adopted. Meanwhile, Nicky beats Milo, Crash and Moose at Anti-Trust. Milo offers to play again to which Nicky agrees, much to Crash and Moose's chagrin.
- Kathleen Wilhoite as Pepper Ann Pearson
- Jeff Bennett as Craig Bean, Heavy Cook, Fool
- Danny Cooksey as Milo Kamalani, Workman #1
- Clea Lewis as Nicky Little
- Pamela Adlon as Moose Pearson
- April Winchell as Lydia Pearson, Abriola Stark, Hawkerwoman
- Don Lake as Sherman Finky, Grumpy Fool, Dashing Man in Black
- Peter MacNicol as Balladeer
- Candi Milo as Constance Goldman, Merchant Woman
- Clive Revill as The Wizard
- Erik von Detten as Guiles/Gary
- Adam Wylie as Crash, Newsboy Kid
(holding a hawk) "Sir Talonsworth!"
(Sir Talonsworth pecks at Nicky)
- The title of this episode is a parody of William Shakespeare's The Merry Wives of Windsor.
- Anti-Trust, as well as how long it takes to play, is a parody of Monopoly.
- Pepper Ann still has her medieval dress from the Romeo and Juliet play she did in the episode "Romeo and Juliet".