Special Guest Stars James Van Der Beek as Dr. Joe Briggs Guest Stars Patch Darragh as Tim Flanagan Margo Martindale as Nurse Klowden Kate Mulgrew as Jeannie Flanagan Peter Gerety as Jimmy Flanagan Michael Chernus as Ryan Flanagan Johnny Hopkins as Bobby Flanagan Kelly Bishop as Lauren Kempton John Ventimiglia as Damiano Fattore Ray Iannicelli as Papa Fattore Morgan Turner as Molly Singer Geraldine Hughes as Tammy Singer Co Starring Tracy Jai Edwards as Pretty Nurse Brit Whittle as Greg Greg Stuhr as Nate Kate Geller as Nurse Nate Lombardi as Angelo