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