Special Guest Stars Paul Rudd as Ben Glenroy Meryl Streep as Loretta Durkin Guest Stars Jackie Hoffman as Uma Heller Jason Veasey as Jonathan Bridgecroft Jesse Williams as Tobert Jeremy Shamos as Dickie Glenroy Linda Emond as Donna DeMeo Ashley Park as Kimber Lee Wesley Taylor as Clifford DeMeo Don Darryl Rivera as Bobo Gerald Caesar as Ty Wessex Allison Guinn as KT Andrea Martin as Joy Payne Lisa Kron as Casting Director Co Starring Teddy Coluca as Lester Willa Dunn as Little Loretta Rosharra Francis as Young Diahann Carroll