The '60s

Josh Hamilton

Michael Herlihy

Julia Stiles

Katie Herlihy

Jerry O'Connell

Brian Herlihy

Jeremy Sisto

Kenny Klein

Jordana Brewster

Sarah Weinstock

Leonard Roberts

Emmet Taylor

Bill Smitrovich

Bill Herlihy

Annie Corley

Mary Herlihy

Donovan Leitch

Neal Reynolds

David Alan Grier

Fred Hampton

Charles S. Dutton

Reverend Willie Taylor

Cliff Gorman

Father Daniel Berrigan

April Mills

Constance

Marc Blucas

Buddy Wells

Jenna Byrne

Melissa

Carnie Wilson

Mama Earth

John C. Meier

Cop #3

David Denman

SDS Radical

Ronald William Lawrence

Civil Rights Leader #1

Kimberly Scott

Althea Taylor

Monti Sharp

Civil Rights Leader #2

Chonique Sneed

Dancer

Sara Van Horn

Sister Elisabeth

Brian Donovan

Chicago Delegate / Reed Student

Raynor Scheine

Sheriff

Gibbs Tolsdorf

Marine

James Arone

Father Monahan

David Paul Needles

Toby Manders

David Tom

Tommy

Lauren Birkell

Joanie

Grant Gelt

Jimmy Dunbar

Lynn Tufeld

Nurse

Ping Wu

Chinese Waiter

Jeremiah Birkett

Marquette

Nigel Thatch

Corey

Elisabeth Röhm

Amanda Stone

Mushond Lee

Huey Newton

Michael Maize

Leather Hat

Hugh Ross

Owl Man

Miranda Bailey

Digger Girl

Steve Eastin

Big Max

Roger Hampton

Half Sauced Man

Tim Reinhard

John Denny

Michael Harney

Tom Gryzbowski

Sean Hennigan

Sergeant

Brian Klugman

Wahoo

Heath Lourwood

WavyGravy

Grant Mathis

FBI Agent #2

Clay Wilcox

Trippie Hippie

Andrew Woodworth

Red

Lorin McCraley

Hippie Guy

Ryan Cutrona

Chairman of Draft Board

James DeBello

O'Doud

Rosanna Arquette

Hippie Mother (uncredited)

Steven Boe

Doctor (uncredited)

Craig Calman

Haight Ashbury Hippie (uncredited)

Johan-Carl Nowack

Freedom Rider Singer

Charles Wheat

Dancer

Philip Cordaro

Singer / Guitar Player on Bus

Carl E. Nelson

Marine Pal

James E. Treloar

Train Engineer

Stan Garner

Train Conductor

Michael Kaufman

Leonard Tannen

Desiree Paterson

Nun

Jennifer Bauerle

Katie's Friend #2

Oded Gross

Berkeley Delegate

Nicky Merchant

Katie's Friend #1

Jason Nesmith

Singer in Band

Mike Williams

Singer in Band

Ryan Chism

Singer in Band

James Michael Marshall

Doorman

William Barillaro

Bus Driver

Terrance Ellis

2nd Blackman

John H. Freeland Jr.

Blackman

Barbara Roberts

Marquette's Mother / Woman in Mississippi

Danny Rogers

Cop #1

Si Paciorek

Clinic Doctor

Bix Barnaba

Hippie in Need

Dana Smith

Bobby Seale

Gregory Storm

David Hillard

Mark Leahy

Reporter #1

Bill Willens

Allen Ginsberg

Austin Marriott

Baby Rainbow

Benjamin Marriott

Baby Rainbow

Shane Barach

Vietnam Vet

Mitch Gibney

FBI Agent #1

Wavy Gravy

Trip Captain

Hannah Whelan

Rainbow (Toddler)

Lou Simon

Panther

James Furlong

Hippie (uncredited)

Eli Jones

Cross-dressing Draftee (uncredited)

Anthony Jordan

Frat House Partier / Dancer (uncredited)

Marcus Le Bov

Hate Ashbury - Hippie (uncredited)

Mindy Miller

Diner Waitress (uncredited)

Michael Emanuel

Coach