In 1944, poet Allen Ginsberg (Daniel Radcliffe) wins a place at Columbia University in New York City. He arrives as a very inexperienced freshman, but soon runs into Lucien Carr (Dane DeHaan), an unruly character who holds strong anti-establishment beliefs.
Ginsberg discovers that Carr only manages to stay at Columbia thanks to a professor working as a janitor, David Kammerer (Michael C. Hall), who writes all of Carr's term papers for him. Kammerer has a predatory relationship with Carr and is in love with him, pressuring Carr for sexual favors in exchange for assuring that he cannot be expelled.