His work on the popular series and his established strength as a comedic actor led to a big screen resurgence, with a featured role in Judge's live-action feature debut "Office Space". As Michael Bolton, an unfortunately named computer programmer for the fictional INITECH Corporation, Herman teamed up with Ajay Naidu to portray friends and co-workers of lead character Peter (Ron Livingston), a programmer who hatches a plan to break out of their corporate malaise after hooking up with disenchanted waitress Joanna (Jennifer Aniston). Sporting a hairstyle and eyeglasses about fifteen years past their prime, and employing the carriage of one beaten into submission, he convincingly and comically portrayed an office peon pushed to the limit.