Weird Science - Season 4 - Eps 24: Pirates!
Wyatt gets the lead role in ""Jolly Roger,"" the school musical. Wyatt has a crush on his leading lady, Jessica, unfortunately she doesn't return his feelings. Lisa tries to make her feel differently, but magic goes awry, and the musical is brought to reality. Now the entire high school is filled with singing pirates and their prisoner, Principal Scampi. Not to mention the fact that they choose a new King, Chett. Not too long after the pirates are discovered, they break out of school in their ship and go about town singing and dancing.
About Weird Science

Title: Weird Science
First Air Date: 1994-03-05
Last Air Date: 1998-07-25
Status: Ended
Rating: 6.682/10 (from 74 votes)
Language: EN
Seasons: 5
Total Episodes: 88
Network: USA Network
Genres: Sci-Fi & Fantasy, Comedy
Production Companies: Universal Television, St. Clare Entertainment, USA Network, Universal Television Entertainment
Synopsis
Gary Wallace, a teenager who dreams of beautiful women and a cheerful life, and his only friend, the shy and geek Wyatt Donnelly, always serve as a target for ridicule and bullying of violent classmates. Once using a computer and mysterious electrical radiation, they manage to bring to life the "woman of their dreams." Her name is Lisa, and she is ready to fulfill the wishes of her creators ...
Cast

Michael Manasseri
Wyatt Donnelly

John Asher
Gary Wallace

Vanessa Angel
Lisa

Lee Tergesen
Chett Donnelly