The Drew Carey Show : The Day the Music Died (1996)
Directed by Gerry Cohen
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Synopsis by Hal Erickson
When the guys' high school band leader Ms. Blankenship dies, a grieving Drew tries to reorganize the old band for a memorial concert. Drew has a special reason for staging this event: it seems that he'd lost his virginity to Ms. Blankenship, as has always regarded himself as her favorite pupil. Imagine Drew's dismay upon learning that he was not the only male student to partake of Ms. Blankenship's "generosity"! Be that as it may, the REAL schocker in this episode concerns Drew's old buddies Kate (Christa Miller) and Oswald (Diedrich Bader).