Brian previously served in the U.S. Army, and has a degree from the fictional Gudger College.

He initially worked at his father-in-law's cracker factory, 'Southern Cracker'(the Dryyyyy Cracker), in middle management. Later he is fired from the factory. Brian's job performance was likely a factor in his dismissal, as his "complete lack of business sense and managerial impotence" caused the number-one cracker company in Milwaukee to fall into a tie for sixth with the dismal "Table Time" and "Allied Biscuit".

Brian moved into a depressing, rundown singles community and tries to start a new career as a singer-songwriter. His demo tape, "Can I Borrow a Feeling?" left Homer in hysterics. ("Can I Borrow a Feeling?" is a real album by Cody Matherson.)

Brian reveals in the episode "I Am Furious Yellow", where he visits his son's school on career day, that he was currently employed as an assistant to the guy who puts fliers under people's windshield wipers. Brian also had a job standing on the curb holding a sign directing people to a condo development and worked as a scarecrow protecting a soy-bean crop, which resulted in his eye being gouged by a crow. Since being fired from the cracker company, Brian seems to be unable to maintain a steady job.