Krusty the Clown is stuck in a rut when the television network pulls his show from the air and his talent agency drops him as a client. But when the Simpsons introduce him to seasoned agent Annie, they are surprised to learn that Annie was Krusty's very first agent. Despite their rocky relationship, Annie is convinced to re-sign Krusty and craft his career comeback. But when Krusty's retro comedy show reboot is deemed a critical success, Krusty must decide to stay with his agent or side with the network executives.