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 Jeremy Shamos as Dickie Glenroy Jesse Williams as Tobert Ashley Park as Kimber Lee Linda Emond as Donna DeMeo Wesley Taylor as Clifford DeMeo Gerald Caesar as Ty Wessex Don Darryl Rivera as Bobo 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