Guest Stars Chris Chalk as Gary Cooper Adina Porter as Kendra James Jane Fonda as Leona Lansing B.J. Novak as Lucas Pruit Jon Bass as Bree Dorrit Joanna Gleason as Nancy Skinner Co Starring Margaret Judson as Tess Westin John F. Carpenter as Herb Wilson Trieu Tran as Joey Phan Thomas Matthews as Martin Stallworth Wynn Everett as Tamara Hart Riley Voelkel as Jennifer "Jenna" Johnson John Hawkinson as Rudy Frank Cermak. as ACN Digital Staffer Luke Jonathan Roumie as Bartender Andrew Collins as Floor Manager Patty Malcolm as Funeral Guest Richie Cottrell as Ned Irina Davidoff as Cleaning Woman Jared Prokop as Bo Christina Blevins as Funeral Guest Nhi Dang as Jenna's Friend Lauren de Miranda as Student