The Simpsons (1989)

S27E17 The Burns Cage

Feeling downcast by Mr. Burns' indifference, Smithers struggles with his emotions as the other characters rally to help him find a boyfriend. At the same time, Milhouse is vying for the lead role in a school performance of Casablanca, competing against a new kid. His motivation? He hopes to share the stage with Lisa, the object of his unreturned affections.