Will Ferrell Harold Crick Maggie Gyllenhaal Ana Pascal Dustin Hoffman Professor Jules Hilbert Emma Thompson Karen Eiffel Queen Latifah Penny Escher Tony Hale Dave Guy Massey IRS Co-Worker #2 T.J. Jagodowski IRS Co-Worker #4 Peter Grosz IRS Co-Worker #5 Tonray Ho IRS Co-Worker #6 Christian Stolte Young Boy's Father Denise Hughes Kronecker Bus Driver Peggy Roeder Polish Woman Danny Rhodes Bakery Employee #1 Linara Washington Bakery Employee #2 Helen Young Bakery Customer #1 Jarrett Sleeper Bakery Customer #4 John Mohrlein Man with Hose Tom Hulce Dr. Cayly Bruce Jarchow Commuter Linda Hunt Dr. Mittag-Leffler Kristin Chenoweth Book Channel Host Bradley Mott Large Man on Bus John M. Watson Sr. TV Author Keith Kupferer Demolition Foreman Danny McCarthy Demolition Crew #1 Tab Baker Demolition Crew #2 Ora Jones Banneker Press Receptionist