The first episode of season 4 is documentary style about the making of Medellin. It shows the troubles of shooting the film and the continued curse of the film. After filming E and Billy Walsh continue their fighting and it gets even more controversial after the Medellin trailer is leaked onto Youtube. Walsh blames E for this. The leak, however, gets the Medellin dreamteam, Vince, Walsh, and E, their new job.

E decides to go into unknown waters and get a new client in Anna Faris. This does not turn out so well being that his loyalty is ultimately with Vince and he cannot ruin Vince's career.

The rest of the gang, Drama and Turtle, get into their usual troubles, usually involving marijuana and women. Ari has trouble getting his son into the school of his choice, and he does everything in his power to get him in.

The last episode of the season the whole gang is in Canne to try and sell their film Medellin to the highest bidder. The film ultimately bombs and gets sold for $1.