Guest Stars Henry Winkler as Eddie R. Lawson Rupak Ginn as Raj Bandyopadhyay Christine Ebersole as Ms. Newberg Michael B. Silver as Ken Keller Stephen Spinella as Russell Berger Bob Gunton as General William Collins Alexandra Socha as Molly O'Shea Lisa Banes as Ellen Collins Michael Mulheren as Jim Harper Kyle Howard as Dr. Paul Van Dyke Maria Dizzia as Cindy Green Marnie Schulenburg as Sherrie Tanner Miriam Shor as Fannie Todd Patti Murin as Ava Bryan Terrell Clark as Officer John Tanner Cloris Leachman as Annette Bellamy Adrienne Warren as Wedding Guest Joshua Bell as Himself Henry Rauch as Martin Co Starring Alysha Umphress as Female Tailor Tom Kitt as Bandleader Daniel Bobby Tuttle as Waiter Jennifer Lamb as Annette Stunt