Guest Stars Ben Feldman as Michael Ginsberg Kevin Rahm as Ted Chaough Mark Moses as Herman "Duck" Phillips Harry Hamlin as Jim Cutler James Wolk as Bob Benson Trevor Einhorn as John Mathis Alexandra Ella as Clara Christine Garver as Moira Channing Chase as Dorothy "Dot" Campbell Sammi Hanratty as Millicent Kathryn Newton as Mandy Liam Aiken as Rolo Paul Rae as Byron Dan Warner as Ray Matthew Iott as Paddy