Rebuffed by a loan officer with high-school ties to Zak (Ray Romano), a desperate Richie (Bobby Cannavale) approaches Maury (Paul Ben-Victor) about doing a deal with Galasso (Armen Garo). Devon (Olivia Wilde) and Ingrid (Birgitte Hjort Sorensen) make the scene at Max's Kansas City, where Devon impresses photographer Billy McVicar (Richard Short) with her ability to charm a major celebrity into giving up his photo.
Tasked by Richie to come up with a new song, Kip (James Jagger) and the Nasty Bits get a crash course in the blues from Lester (Ato Essandoh). Andrea (Annie Parisse) fires a longtime American Century employee, angering Richie. Clark (Jack Quaid) finds musical enlightenment from Jorge (Christian Navarro), his onetime mailroom nemesis.
