Joe, Samantha, and David seek help from Ellen (Joe's mother), and neighbor Wanda, who is leader of the local historical society, in the mystery of the man digging up the unknown grave in the park; Wishbone continues as Tom Sawyer.
The kids help put on a traditional story-telling show to raise money. David's Uncle Homer is the star and throughout the episode, tells verbal African folk tales. Wishbone plays the part of Anansi and others in the folk tales.
Wishbone takes on the 'prominent' role of Cyrano de Bergerac as the kids have to study poetry in school. David struggles the most with having to write his own poem and uses his own anonymous Cyrano to cheat.
A stray dog is causing trouble in the neighborhood and Wishbone is getting the blame. As Joe, Sam, and David try to track the dog down, Wishbone is reminded of Sherlock Holmes and the Hound of Baskervilles.
Joe, Ellen and Wishbone meet a woman who lived in their home over 40 years ago, who comes to see the house and find the treasures she left behind as a kid. Wishbone imagines himself as Rip Van Winkle who falls asleep for 20 years and doesn't recognize anything or anybody, and can't get anyone to believe who he is.
Joe runs into a shady businessman at the town fair who's marketing a new virtual reality helmet that sucks Joe into a different world. This reminds Wishbone of Faust, a scholar who traded his soul to the devil for fun, but everything he wants comes at a price.
Wishbone becomes the magical Ali Baba in Scheherazade's Arabian Nights. The trio gets into trouble with a new computer and Wanda loses her purse. David's sister, Emily, finds it but doesn't want to return it.
Wanda finds a fresh experience with a new man, leaving Bob Pruitt to wonder what's going on and causing him to act out of the ordinary. The shift in personality is mirrored in Wishbone's telling of Jekyll and Hyde as the title character's friend, Gabriel John Utterson.
Joe's highly allergic friend Nathaniel stays at the Talbots' for the weekend but his overprotective mother announces he's allergic to dogs so Wishbone has to stay in the yard. Wishbone likens Nathaniel's affliction to that of Argon in Moliere's play The Imaginary Invalid, whose family convince him he's sick so they can collect his inheritance.
Wishbone plays C. Auguste Dupin in Poe's 'The Purloined Letter'. Joe has a crush on a teacher and a classmate, Curtis, sees Joe writing a love note, which ends up in the teacher's hands. Will Joe be able to get it back before she reads it or Curtis uses it against him?
Joe thinks using a calculator instead of his own mind will help him do better in math. Meanwhile, Wishbone as The Time Traveler in H.G. Wells' The Time Machine, travels to the year 802701 A.D. and finds the human race has diminished all forms of intelligence.
Wishbone is Robin Hood as Joe helps a cafeteria worker friend break the rules to help others. They get caught by the stern director who cares more about time and money than charity and Wishbone distracts him as they get away. But that isn't the end of their problems.
Wishbone and Joe live parallel stories of experiencing how the other half lives in this adaptation of 'The Prince and the Pauper'. Joe believes he'd be better at coaching than the coach, so he gets his shot to prove it.
'The Count of Monte Cristo' and Edmond Dantes are brought to life by Wishbone as David builds a snow machine that Damont uses to make trouble. But the revenge David and the others take is not the best path.
Samantha enlists Joe and David's help to find a legendary horseshoe in a condemned barn before it's torn down. Wishbone plays Jim Hawkins in Treasure Island, where he also encounters dangerous obstacles to search for a great treasure.
Wishbone delivers the Biblical story of David and Goliath. Meanwhile, Joe and Ellen go on a trip and leave Wishbone with David's family. Emily and David both cause some trouble, but David's is dangerous and destructive. He must tell the truth before it gets worse.
Somebody has secretly taken embarrassing pictures of Sam and posted them all over the school and signing an alias to his fliers. Sam, Joe and David try to figure out who the mysterious photographer is while Wishbone plays Sherlock Holmes, going in disguise to retrieve a stolen photograph in Sir Arthur Conan Doyle's "A Scandal in Bohemia".
Joe starts hanging with a new bunch of guys, ignoring Sam and David, and even Wishbone. He starts to imitate the behavior of his new friends and soon realizes it could cost him his best friends. Wishbone imagines himself as Henry Fleming, a boy who also takes on more than he can handle when he goes off to fight in the Civil War in The Red Badge of Courage.
The school is putting on a production of Shakespeare's The Tempest, with David directing, Joe working as stage manager, and Sam as Miranda. Meanwhile, in the fantasy sequences, Wishbone portrays Ariel in the same play.
Ellen befriends a young man who has recently lost his own mother, which causes Joe to wrestle with his jealousy. To help him, Senora Julia, an old friend who is like a second mother to him, tells him the story of Juan Diego (played by Wishbone, of course) and Our Lady of Guadalupe.
Joe starts a grocery delivery business, but learns that his single-minded pursuit of money could cost him his friendship with Sam and David. In the fantasy sequence, Wishbone tells the story of Midas and his golden touch.
Wishbone becomes a Native American warrior in the Dakota tale told by visiting storyteller Lee Natonabah. Joe and David volunteer to tell their own family stories as well at a story-telling performance, which leads to Joe feeling inadequate in his father's shadow.
In a recap of many of the episodes, Wishbone is one again everyone from Tom Sawyer to Oliver Twist. Wanda leaves a friend's dog with the Talbots, for them to dog-sit, and Wishbone tries to entertain her by re-telling his favorite stories.