Josh Hamilton as Michael Herlihy

Julia Stiles as Katie Herlihy

Jerry O'Connell as Brian Herlihy

Jeremy Sisto as Kenny Klein

Jordana Brewster as Sarah Weinstock

Leonard Roberts as Emmet Taylor

Bill Smitrovich as Bill Herlihy

Annie Corley as Mary Herlihy

Donovan Leitch as Neal Reynolds

David Alan Grier as Fred Hampton

Charles S. Dutton as Reverend Willie Taylor

Cliff Gorman as Father Daniel Berrigan

April Mills as Constance

Marc Blucas as Buddy Wells

Jenna Byrne as Melissa

Carnie Wilson as Mama Earth

John C. Meier as Cop #3

David Denman as SDS Radical

Ronald William Lawrence as Civil Rights Leader #1

Kimberly Scott as Althea Taylor

Monti Sharp as Civil Rights Leader #2

Chonique Sneed as Dancer

Sara Van Horn as Sister Elisabeth

Brian Donovan as Chicago Delegate / Reed Student

Raynor Scheine as Sheriff

Gibbs Tolsdorf as Marine

James Arone as Father Monahan

David Paul Needles as Toby Manders

David Tom as Tommy

Lauren Birkell as Joanie

Grant Gelt as Jimmy Dunbar

Lynn Tufeld as Nurse

Ping Wu as Chinese Waiter

Jeremiah Birkett as Marquette

Nigel Thatch as Corey

Elisabeth Röhm as Amanda Stone

Mushond Lee as Huey Newton

Michael Maize as Leather Hat

Hugh Ross as Owl Man

Miranda Bailey as Digger Girl

Steve Eastin as Big Max

Roger Hampton as Half Sauced Man

Tim Reinhard as John Denny

Michael Harney as Tom Gryzbowski

Sean Hennigan as Sergeant

Brian Klugman as Wahoo

Heath Lourwood as WavyGravy

Grant Mathis as FBI Agent #2

Clay Wilcox as Trippie Hippie

Andrew Woodworth as Red

Lorin McCraley as Hippie Guy

Ryan Cutrona as Chairman of Draft Board

James DeBello as O'Doud

Rosanna Arquette as Hippie Mother (uncredited)

Steven Boe as Doctor (uncredited)

Craig Calman as Haight Ashbury Hippie (uncredited)

Johan-Carl Nowack as Freedom Rider Singer

Charles Wheat as Dancer

Philip Cordaro as Singer / Guitar Player on Bus

Carl E. Nelson as Marine Pal

James E. Treloar as Train Engineer

Stan Garner as Train Conductor

Michael Kaufman as Leonard Tannen

Desiree Paterson as Nun

Jennifer Bauerle as Katie's Friend #2

Oded Gross as Berkeley Delegate

Nicky Merchant as Katie's Friend #1

Jason Nesmith as Singer in Band

Mike Williams as Singer in Band

Ryan Chism as Singer in Band

James Michael Marshall as Doorman

William Barillaro as Bus Driver

Terrance Ellis as 2nd Blackman

John H. Freeland Jr. as Blackman

Barbara Roberts as Marquette's Mother / Woman in Mississippi

Danny Rogers as Cop #1

Si Paciorek as Clinic Doctor

Bix Barnaba as Hippie in Need

Dana Smith as Bobby Seale

Gregory Storm as David Hillard

Mark Leahy as Reporter #1

Bill Willens as Allen Ginsberg

Austin Marriott as Baby Rainbow

Benjamin Marriott as Baby Rainbow

Shane Barach as Vietnam Vet

Mitch Gibney as FBI Agent #1

Wavy Gravy as Trip Captain

Hannah Whelan as Rainbow (Toddler)

Lou Simon as Panther

James Furlong as Hippie (uncredited)

Eli Jones as Cross-dressing Draftee (uncredited)

Anthony Jordan as Frat House Partier / Dancer (uncredited)

Marcus Le Bov as Hate Ashbury - Hippie (uncredited)

Mindy Miller as Diner Waitress (uncredited)

Michael Emanuel as Coach