| Will Armstrong | Ensemble | |
| Brad Aspel | Andy Lee | |
| Greg Beck Broadway debut | Oscar | |
| Graham Bowen | Ensemble | |
| Celina Carvajal | Annie | |
| Patrick Cassidy | Julian Marsh | (May 7, 2004-Jan 2, 2005) |
| Erin Crouch | Diane | |
| Ensemble | ||
| Michael Dantuono | Pat Denning | |
| Julian Marsh | (May 28, 2002-Jun 20, 2002) | |
| Julian Marsh | (Aug 12, 2003-Aug 14, 2003) | |
| Brad DeLima Broadway debut | Ensemble | |
| Amy Dolan | Annie | (Jun 11, 2002 - ?) |
| Angie Everett | Ensemble | |
| Luis Figueroa | Ensemble | |
| Emily Fletcher | Ensemble | |
| Jonathan Freeman | Bert Barry | |
| Kristin Gaetz | Ensemble | |
| Melissa Giattino | Ensemble | |
| Susan Haefner | Ensemble | |
| Brad Hampton | Ensemble | |
| Waiter | ||
| Nadine Isenegger | Peggy Sawyer | (Dec 17, 2002 - ?) |
| Kolina Janneck | Ensemble | |
| Sarah L. Johnson | Ensemble | |
| Shirley Jones | Dorothy Brock | (May 7, 2004-Aug 8, 2004) |
| Angela Kahle Broadway debut | Ensemble | |
| Amy F. Karlein | Ensemble | |
| Regan Kays Broadway debut | Ensemble | |
| Natalie King Broadway debut | Ensemble | |
| Matt Lashey | Ensemble | |
| Beth Leavel | Dorothy Brock | (Jun 11, 2002 - ?) |
| Alison Levenberg Broadway debut | Ensemble | |
| Kate Levering | Peggy Sawyer | (Aug 30, 2002-Dec 15, 2002) |
| Gavin Lodge | Ensemble | |
| Partial Swing | ||
| Thug | ||
| Steve Luker | Doctor | |
| Mac | ||
| Thug | ||
| Patti Mariano | Maggie Jones | |
| Peter Marx | Andy Lee | (Apr 2003-Jul 2003) |
| Joni Michelle Broadway debut | Ensemble | |
| Amy Miller Broadway debut | Ensemble | |
| Sarah Misiano Broadway debut | Ensemble | |
| Karen Murphy | Maggie Jones | |
| Joel Newsome | Bert Barry | |
| Ensemble | ||
| Waiter | ||
| Amy Palomino Broadway debut | Ensemble | |
| Tony Palomino Broadway debut | Ensemble | |
| Alison Paterson | Ensemble | |
| Partial Swing | ||
| Meredith Patterson | Peggy Sawyer | (Aug 18, 2001-Aug 18, 2002) |
| Darin Phelps | Waiter | |
| Wes Pope | Ensemble | |
| Richard Pruitt | Abner Dillon | |
| Frank Root | Bert Barry | |
| Blair Ross | Dorothy Brock | (Aug 10, 2004-Jan 2, 2005) |
| Alana Salvatore Broadway debut | Annie | |
| John James Scacchetti Broadway debut | Ensemble | |
| Joni Michelle Schenck | Ensemble | |
| Megan Schenck | Phyllis | |
| Jennifer Leigh Schwerer | Diane | |
| Ensemble | ||
| Eric Sciotto | Ensemble | |
| Waiter | ||
| Cindy Shadel Broadway debut | Ensemble | |
| Kelly Sheehan | Lorraine | |
| Kristyn D. Smith | Ensemble | |
| Vanessa Sonon | Ensemble | |
| Patrick Ryan Sullivan | Julian Marsh | (Aug 15, 2003 - ?) |
| Will Taylor Broadway debut | Ensemble | |
| Erika Vaughn | Partial Swing | |
| Josh Walden | Ensemble | |
| Bob Walton | Bert Barry | |
| Nikki Williams Broadway debut | Ensemble | |
| Tom Wopat | Julian Marsh | (Jun 21, 2002-Aug 10, 2003) |
| Kevin B. Worley | Ensemble | |
| Partial Swing | ||
| Ericka Yang | Ensemble | |
| Ethel |