Bart learns of a legendary prankster (voice of Jonah Hill) from Springfield Elementary's past and becomes fast friends with the joker, who's now 19 years old and hasn't stopped doing pranks.
Moe gets Homer to be his wingman, but becomes distraught when the women are drawn to Homer as well. Meanwhile, Marge discovers some gray hairs and tries a new more mature hair style to go along with it, much to Bart’s dismay.
Bart’s Angry Dad comic is turned into a movie and becomes a critics’ recommendation. Each time the movie wins something, Homer takes credit for each time.
Homer’s rage toward Bart gets him in trouble with a therapist (Paul Rudd) who manages to reverse Bart and Homer’s roles. Kareem Abdul-Jabbar has a voice cameo as himself.