"Listen Up Philip" is about one of those vampiric souls who suck the life out of everybody around them, Philip Friedman (Jason Swartzman). He is a young writer living in New York City, having just finished his second novel. Friedman begins the movie discovering just how wonderful it feels to verbally abuse his ex-girlfriend and former roommate, then never becomes more charming. He ignores and alienates his current lover, Ashley (Elisabeth Moss), he systemically destroys his writing career in Manhattan, and continues to validate himself on his own greatness as compared to the mediocrity of the world around him. Philip is an unlikable protagonist, yet "Listen Up Philip" is a sympathetic and fascinating character study within a black comedy.
Much of "Listen Up Philip" is a tale of loneliness in its three main characters thanks to Philip's clumsy destructiveness. Ashley and Philip never have a formal break up, because Philip is too much of a swine to allow the final conversation to take place. Yet Ashley spends her summer in miserable torment thanks to this man she loved. Philip's mentor, the great author, Ike Zimmerman (Jonathan Pryce) allows Philip to live with him upstate. Ike then sees Philip repeat the same antisocial behavior as he did in his prime, and suddenly comes to realize how terribly alone he has become. Philip himself spends his autumn banished away to an upstate college teaching Creative Writing, where he ruins yet another relationship, and in his quiet isolation, unable to understand the people from he is estranging himself.