Guest Stars Daniel Sauli as Tommy Longo Olivia Luccardi as Melissa Andrea-Rachel Parker as Bernice Kim Director as Shay Method Man as Rodney Ralph Macchio as Officer Haddix Jamie Neumann as Ashley David Krumholtz as Harvey Wasserman Thaddeus Street as Black Frankie Don Harvey as Danny Flanagan Anwan Glover as Leon Aaron Dean Eisenberg as Todd Lang Kayla Foster as Barbara Genevieve Hudson-Price as Jocelyn Pernell Walker as Ruby "Thunder Thighs" Ari Kappatos as George Michael Kostroff as Rizzi Gino Vento as Carlos Ngozi Anyanwu as Rochelle Tariq Trotter as Jerry Love Saul Stein as Marty Hodas Garry Pastore as Matty "The Horse" Shaun O'Hagan as Lieutenant Gerald Sweeney E.J. Carroll as Fat Mooney Ed Moran as Capt. Peter McDonagh James Ciccone as Carmine Patriccia Danielle Burgess as Tiffany John Paul Harkins as TBD Kate Levy as Harriet Parker Brian McCarthy as Greg Colin Moss as Well-Heeled John Kersti Bryan as Connie Jack Gindi as Salesman Joe Danny Zuhlke as TBD Jay Ferraro as Raincoater #1 Nick Addeo as Raincoater #2 Ryan Bauer-Walsh as Fan #1 Hayden Clifton as TBD Deborah Twiss as Mindy Jacklyn Collier as TBD Malachy Cleary as TBD Matt Giroveanu as TBD Charlie Fersko as TBD David T. Zimmerman as Businessman Nicholas Feitel as Nervous John Kendall Lloyd as Man in Suit Stephen DeRosa as Factory Manager John Dinello as Vinny "The Chin" Gigante