At the conclusion of season four last September, the boys had little hope or money after a disastrous screening of the movie "Medellin" at the Cannes Film Festival. In season five, Vince must find a way to rejuvenate his career. His best friend and manager Eric is determined to get Vince back to the top, while struggling with his expanding management company. Agent Ari Gold, who is having a few career conflicts of his own, struggles to deliver for Vince, given the current state of things. Drama, meanwhile, continues his successful television career while experiencing problems in his love life, and Turtle is forced to reexamine his contribution to it all.