As Season 4 unfolds, Larry (Garry Shandling) finds himself dealing with the fallout from a series of dubious romances involving guests Rosanne and Rosie Perez, a network publicist and an eighteen-year-old college intern from his alma mater, the University of Minnesota. Larry's romantic escapades don't stop there as both he and Hank (Jeffery Tambor) end up in bed with his ex-wife Jeannie. As Hank questions his own hiring of a gay assistant and Artie brings an ex-con and recovering drug addict onto the staff, Larry gets some surprising news after a series of bounced checks reveal that he's nearly bankrupt. But problems that include a rash of guest cancellations, charges of racism, and a star-struck staff take a backseat when, as Larry is away on "vacation" for some plastic surgery, guest host Sandra Bernhard tries to engineer a coup that will make the post permanent.