I've never had a terrible job, I've loved every single one I've ever had.
1. Little League Umpire -- No better way to spend spring/summer in high school than to get paid to be out on the diamond.
2. Roofer Grade B -- Spent three summers in college working for Boeing on their summer roofing crew. Absolutely awesome summer job, making $18/hour and overtime every other weekend (1.5x pay on Saturday, 2x pay on Sundays, and 3x on July 4th and Labor Day).
3. Administrative Assistant -- Worked in the IT Outsourcing branch of a large insurance company in Seattle for two summers during graduate school. Working with the CEO/CIO as well as technical writers gave me a nice glimpse of the business world.
4. School Psychologist -- Current job which I plan to have until I retire. I come to work everyday excited about working with children and trying to be a positive agent of change. I couldn't ask for a better job.