- Patrick Brennan - Earl
- Elizabeth Gillies - Young Jenny
- Kate Mulgrew - Helen Donnelly
- Jason Furlani - George
- Kenny Marino - McGee
- Chris Bauer - Huey Farrell
- Mark Margolis - Sal Minetta
- Lenny Venito - Benny Cool
- Ned Eisenberg - Frankie Stein
- Paul Calderon - Detective at Prison
- Joseph D'Onofrio - Louie Downtown
- Frank Page - Richie
- Adelia Saunders - Kim
- Max Miner - Tommy Donnelly - Age 8
- Sonny Marinelli - Detective Sunny
- Jay Spadaro - Michael Hogan
- Audrie Neenan - Gertie
- Richard Petrocelli - Italian Soldier #1
- John Cenatiempo - Italian Soldier #2
- Glenn Taranto - Guy at Counter
- Kathleen Doyle - Helen Donnelly
- Dylan Hartigan - Young Joey
- Daniel Manche - Kid
- Lee Sellars - Man
- Frank Bonsangue - Wiseguy
- Maria Di Angelis - Interrogation Cop
- Allan Steele - Domenic Calero
- Allan Steele - Detective Calero
- Olja Hrustic - Flirting Girl
- Che Landon - Rosie Maxwell
- Denis McKeown - Pallbearer
- Sean Patrick Reilly - Mel Donnelly
- Lauren Bittner - Mary Ann Maxwell (uncredited)
- Sean Cory - Store Owner (uncredited)
- Greg D'Agostino - Italian Soldier #3 (uncredited)
- Seamus Davey-Fitzpatrick - (uncredited)
- Dominick Mancino - Mobster (uncredited)
- David C. Roehm Sr. - Gurney Patient (uncredited)
- Christopher Shand - (uncredited)
- Andrea Bertola Shaw - Street Walker (uncredited)
- Kevin Conway - Jenny's Pop
- Sherri Parker Lee - Lisa Tyler
- Bradley White - Ed
- Richard Topol - Doctor
- Laurence Blum - Nervous Lowlife
- Betsy Beutler - Joanie
- Kevin Cannon - Westie
- Bonnie Discepolo - Nosy Neighbor
- Kenny Shapiro - Lawyer
- Brian Donahue - Jackie (uncredited)
- Keith Moyer - Hospital Visitor (uncredited)
- John Bolger - Bobby Donnelly
- John Bolger - Bobby Donnelly (uncredited)
- Ken Garito - Anthony Lino
- Tom Riis Farrell - Building Inspector Ferguson
- Erika Michels - Prison Nurse
- Chance Kelly - Paddy
- Michael Rispoli - Alo
- Michael Rispoli - Alo (uncredited)
- Geoffrey Wigdor - Tommy 'Teach' Corcoran
- Anthony Grasso - Building Department Clerk
- Elizabeth Regen - Mia
- Harris Doran - Book Store Clerk
- Chris Kipiniak - Sharkey
- John Juback - Leo the Bartender
- John Juback - Leo
- James Badge Dale - Samson
- Wass Stevens - Dickie
- Nick Damici - Ray
- Kate Nowlin - Doctor
- John-Luke Montias - Detective
- Denise Pleune
- Bobby Moresco
- Alexa L. Fogel
- Jeff King
- James Bigwood
- Sean Whitesell
- Mark Isham
Jonathan Tucker interpreta a Tommy Donnelly en la serie.
Tom Guiry interpreta a Jimmy Donnelly en la serie.
Olivia Wilde hace el papel de Jenny Reilly.
Billy Lush interpreta a Kevin Donnelly en la serie.
Michael Stahl-David interpreta a Sean Donnelly en la serie.
Kirk Acevedo interpreta a Nicky Cottero en la serie.
Keith Nobbs hace el papel de Joey 'Ice Cream'.
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