- Ron Livingston as Peter Gibbons
- Jennifer Aniston as Joanna
- Stephen Root as Milton Waddams
- Gary Cole as Bill Lumbergh
- John C. McGinley as Bob Slydell, a business consultant
- David Herman as Michael Bolton
- Ajay Naidu as Samir Nagheenanajar
- Diedrich Bader as Lawrence, Peter's next-door neighbor
- Michael McShane as Dr. Swanson
- Richard Riehle as Tom Smykowski
- Alexandra Wentworth as Anne
- Greg Pitts as Drew, a young employee at Initech
- Paul Willson as Bob Porter, Bob Slydell's colleague
- Todd Duffey as Brian, Chotchkie's Waiter; an overly cheerful young man who works at Chotchkie's with Joanna
- Orlando Jones as Steve, a magazine salesman and former employee at Initrode
- Mike Judge as Stan, the manager of the Chotchkie's restaurant
- Joe Bays as Dom Portwoid, one of Peter's superiors at Initech
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