Daniel Radcliffe as Allen Ginsberg

Dane DeHaan as Lucien Carr

Michael C. Hall as David Kammerer

Jack Huston as Jack Kerouac

Ben Foster as William Burroughs

David Cross as Louis Ginsberg

Jennifer Jason Leigh as Naomi Ginsberg

Elizabeth Olsen as Edie Parker

John Cullum as Professor Steeves

Brenda Wehle as Permissions Librarian

Erin Darke as Gwendolyn

Craig Chester as Businessman

Lenore Harris as DA Secretary

Mark Ethan as Campus Guard

Zach Appelman as Luke Detweiler

David Rasche as Dean

Quinlan Corbett as Billeting Officer

Dawn Newman as Jazz Singer

Clancy O'Connor as Tour Guide

Jon DeVries as Mr. Burroughs

Leslie Meisel as Edith Cohen

Sarah Hollis as Harlem Club Patron

Nicole Signore as Page

Olen Holm as Sailor

Michael Cavadias as Ray Conklin

Kyra Sedgwick as Marian Carr (uncredited)

Laura Obiols as Kristina Laakson (uncredited)

Colin Michael Walker as Columbia Classmate (uncredited)

Kevyn Settle as Norman (uncredited)

Martin Pfefferkorn as 1940s Prisoner (uncredited)

Anna Kuchma as Interracial Couple (uncredited)

Sean Grady as Barfly (uncredited)

Matt Giroveanu as Luke's Friend #1 (uncredited)

Nick Diamantis as Merchant Marine (uncredited)

Jonathan Cantor as Ogden Nash (uncredited)

Ranardo Domeico Grays as Jazz Club Patron (uncredited)