Tommy Donnelly

Jonathan Tucker

Nicky Cottero

Kirk Acevedo

Jenny Reilly

Olivia Wilde

Jim Donnelly

Thomas Guiry

Kevin Donnelly

Billy Lush

Joey `Ice Cream'

Keith Nobbs

Sean Donnelly

Michael Stahl-David

Guest Star

Pablo Schreiber

Guest Star

Michael Rispoli

Guest Star

John Lavelle

Derek 'Dokey' Farrell

Peter Greene

Guest Star

Betsy Beutler

Guest Star

Peter Gerety

Guest Star

Harry O'Reilly

Vinnie Culiari

Brian Tarantina

Guest Star

James Badge Dale

Earl

Patrick Brennan

Guest Star

Dick Latessa

Frankie Stein

Ned Eisenberg

Helen Donnelly

Kate Mulgrew

Young Jenny

Elizabeth Gillies

Jenny's Pop

Kevin Conway

Jimmy Donnelly - Age 11

Jimmy Walsh

Guest Star

Molly Schaffer

Guest Star

Seamus Davey-Fitzpatrick

Tommy Donnelly - Age 8

Max Miner

Mel Donnelly

Sean Patrick Reilly

Guest Star

Kevin Corrigan

Kevin Donnelly - Age 8

T.J. Stanton

Nadine

Jamie Bonelli

Bobby Donnelly

John Bolger

Louie Downtown

Joseph D'Onofrio

Kim

Adelia Saunders

Sean Donnelly - Age 7

Lance Michael Schaefer

Detective Calero / Domenic Calero

Allan Steele

Sharkey

Chris Kipiniak

Leo / Leo the Bartender

John Juback

George

Jason Furlani

McGee

Kenny Marino

Huey Farrell

Chris Bauer

Sal Minetta

Mark Margolis

Benny Cool

Lenny Venito

Detective at Prison

Paul Calderon

Richie

Frank Page

Detective Sunny

Sonny Marinelli

Michael Hogan

Jay Spadaro

Guy in Bar

Jude Moresco

Gertie

Audrie Neenan

Italian Soldier #1

Richard Petrocelli

Italian Soldier #2

John Cenatiempo

Guy at Counter

Glenn Taranto

Helen Donnelly

Kathleen Doyle

Young Joey

Dylan Hartigan

Kid

Daniel Manche

Man

Lee Sellars

Wiseguy

Frank Bonsangue

Interrogation Cop

Maria Di Angelis

Flirting Girl

Olja Hrustic

Rosie Maxwell

Che Landon

Pallbearer

Denis McKeown

Pallbearer #2

Michael Phelan

Lisa Tyler

Sherri Parker Lee

Ed

Bradley White

Doctor

Richard Topol

Nervous Lowlife

Laurence Blum

Chloe

Michele Hayes

Westie

Kevin Cannon

Nosy Neighbor

Bonnie Discepolo

Lawyer

Kenny Shapiro

Anthony Lino

Ken Garito

Building Inspector Ferguson

Tom Riis Farrell

Prison Nurse

Erika Michels

Paddy

Chance Kelly

Tommy 'Teach' Corcoran

Geoffrey Wigdor

Building Department Clerk

Anthony Grasso

Mia

Elizabeth Regen

Book Store Clerk

Harris Doran

Dickie

Wass Stevens

Ray

Nick Damici

Doctor

Kate Nowlin

Detective

John-Luke Montias

Police Officer

Keith Markey

Thug

Tom Verri