I've been thinking about this one, and I really don't think I've had a job that I absolutely hated. Sure there's been positives and negatives about the ones I've had, but overall they were fun:
Age 14-15 -- Paper route...easy first job.
Age 15-17 -- I had a summer job working at a camp ground. I liked the group I worked with and we did a lot of various maintenance stuff...the worst part of that was cleaning out septic tanks on various trailers...but it didn't take too long and the pump did most of the work.
Age 17-22 -- I worked at a bowling alley doing pinchaser/maintenance. Long hours and stuff, but I got to bowl for free and the people I worked with were great.
Age 19-22 -- I had a summer job working as a teacher's aid with multiply-handicapped children. It would wipe me out, but it was extremely rewarding work.
Age 20-21 -- I worked as night security for the dorms at UCF. It gave me time to study and I was a bit of a nightowl at the time.
Age 22-present -- US Air Force. Starting out as an A!C and working my way up to Captain I've had several jobs and assignments:
'93-99 -- After basic training and tech school, I worked as an Autotracking radar journeyman. It was a neat job because we maintained and operated radars that simulated AAA and SAMs. We would lock up on the fighters and give them a realistic training environment by "shooting them down". To be truly effective at the job we had to learn enemy weapons and tactics. Not something I thought I'd be doing in an electronics career field. Plus we were stationed on the outer banks of North Carolina. I plan on possibly retiring there someday.
'99-02 -- I was reassigned to Eielson AFB, Alaska! Since my Autotrack job was being contracted out, my primary duty there was Quality Assurance Evaluator (QAE). I wasn't too fond of watching contractors do my job, but luckily, we had additional duties of range improvement and various other engineering projects, plus we hosted COPE THUNDER -- PACAF's premier inter-service exercise. I got to be involved in planning and executing an air war from beginning to end, plus I got to work with various different units and even foreign services! Add to that I got to ride around the Alaska interior on track vehicles, 4-wheelers, snow machines, and even by helicopter! I was in heaven! I also would love to move back there someday!
'02-03 -- After getting my BS degree from University of Alaska Fairbanks, I went to OTS and spent a year training as a space and missile officer at Vandenberg AFB, California. It's a great area, and the surfing's better than the East Coast, but I was eager to get back to the operational world. Still, I had a lot of fun there.
'03-07 -- I was a missile officer at FE Warren AFB, WY. I loved the first two years as part of the 400th Missile Squadron. I pulled combat alert duty with the Peacekeeper weapon system. We also deactivated that weapon system as part of a treaty with the Russians. I worked with some of the most team-oriented people ever, plus it was my third, small-unique unit I've been in and loved how everyone took care of eachother. After the deactivation, I went to the Minuteman II weapon system. The teamwork aspect just wasn't as prevalent as it was in PK, add to that I worked for a commander that I did not really like or respect, it made the second half of my tour there a lot tougher. I still worked with some great people, and it was probably one of the most important jobs I've had, so I still liked it overall. Plus, I lived in Ft Collins, Co where I met my wife and got to meet a couple of Forum Members!

'07 -- present -- After a 4 month stint at Vandenberg, I am now a Mission Commander for the 2nd Space Operations Squadron at Schriever AFB, Co. We do all the command and control of the GPS constellation. The crew life is better than missiles, and I work with a great team of enlisted and officers, plus the location is awesome! We have a great house, with an awesome view of the Rockies (Pike's Peak in particular), plus a shorter commute than I had from Ft Collins to Cheyenne. My only regret is I am trading off a technical role for a leadership one. I'm learning all I can about what these satellites do as well as the systems that control them, but being the crew leader is also fun.