Drake & Josh (2004)

S2E11 The Mean Teacher

Drake is stuck in a relationship with his girlfriend Kelly, who can't stop laughing, and he desperately wants to end things. However, he’s caught in a bind because she’s the daughter of his strict teacher, Mrs. Hayfer, who warns him of summer school if he dares to break up with Kelly. On the side, Josh proudly sports an incredibly hideous shirt, convinced it brings him good luck.