| James Gandolfini | Tony Soprano |
| Lorraine Bracco | Dr. Jennifer Melfi |
| Edie Falco | Carmela Soprano |
| Michael Imperioli | Christopher Moltisanti |
| Steven Van Zandt | Silvio Dante |
| Tony Sirico | Paulie 'Walnuts' Gualtieri |
| Robert Iler | A.J. Soprano |
| Jamie-Lynn Sigler | Meadow Soprano
(as Jamie-Lynn DiScala) |
| Drea de Matteo | Adriana La Cerva |
| John Ventimiglia | Artie Bucco |
| Steve Buscemi | Tony Blundetto |
| Jerry Adler | Hesh Rabkin |
| Robert Loggia | Feech La Manna |
| Peter Bogdanovich | Dr. Elliot Kupferberg |
| David Strathairn | Robert Wegler |
| Frankie Valli | Rusty Millio |
| Joe Santos | Angelo Garepe |
| Ray Abruzzo | Carmine Lupertazzi Jr. |
| John Pleshette | Dr. Ira Fried |
| Frank Vincent | Phil Leotardo |
| Patti D'Arbanville | Lorraine Calluzzo |
| Carl Capotorto | Little Paulie Germani |
| David Lee Roth | David Lee Roth |
| Lawrence Taylor | Lawrence Taylor |
| Bernie Brillstein | Bernie Brillstein |
| Max Casella | Benny Fazio |
| Joseph R. Gannascoli | Vito Spatafore |
| Joe Maruzzo | Joe Peeps |
| Michael Pemberton | Supervisor Jimmy Curran |
| Stewart J. Zully | Alan Ginsberg |
| Will Janowitz | Finn DeTrolio |
| David Little | Asa Silverman |
| Leon Wieseltier | Stewart Silverman |
| Chris Caldovino | Billy Leotardo |
| Cameron Boyd | Matt Testa |
| Cal Robertson | Andrew |
| Adam Rose | Todd |
| Gabriel Millman | Lem |
| Michael Goldstrom | Jonah Dangler |
| Vincenzo Ameruoso | Carl 'Fat Carl' Carlo |
| Frank Fortunato | Jason Evanina |
| Anthony Desio | Jimmy La Manna |
| Terence Winter | Tom Amberson
(as Terence Patrick Winter) |
| Fran Gennuso | Ms. Mary Bisacci |
| Manu Narayan | Sukhjit Khan |
| Lenny Singer | Uncle Jack |
| Susan Pourfar | Gillian |
| Dennis Aloia | Justin Blundetto |
| Kevin Aloia | Jason Blundetto |
| Joseph La Rocca | Rich Alberga
(as Joseph Larocca) |
| Gina Lynn | Stripper |
| John Marinacci | Dealer |
| Jimmy DellaValle | Gunman
(as Jimmy Della Valle) |
| John Lanzillotto | Mook |
| Victor Cruz | First Valet |
| Jorge Pupo | Second Valet |
| Gillien Goll | Guest |
| Neil Levine | Another Guest |
| Valerie Romanoff | Band Leader |
| Chioma Chidebeln-Eze | Starlight Orchestra |
| Caren Cole | Starlight Orchestra |
| Andrea Eigner | Starlight Orchestra |
| Erin Henry | Starlight Orchestra |
| Allison Miller | Starlight Orchestra |
| Deborah Pilley | Starlight Orchestra |
| Sue Terry | Starlight Orchestra |
| Susan Terwilliger | Starlight Orchestra |
| Salma Hayek | Frida Kahlo
(archive footage) (uncredited) |
| Keith Leonard | Bar Patron
(uncredited) |
| Alfred Molina | Diego Rivera
(archive footage) (uncredited) |
| Danny Petrillo | Teenage Tony Soprano
(uncredited) |
| Alicia Regan | Cousin
(uncredited) |