I had two great jobs. One as a medical tech in a hospital that was great until the administration changed and started screwing with the hired help and then as an over night courier for the #2 express company, hired on by a great subcontractor who had just taken over the area. Not only did he patiently teach me what to do, he never got pissed at my errors, supported me against the home office, and let me do my thing. That was MCL freight and the boss was Mike Little. Best boss I ever had.
My best job ever was working in a butcher shop (serving) when I was in high school. The people were brilliant, and we had so much fun, that the shifts flew by. They still ask after me, almost six years later. I still drop in and spend half an hour with them when I can.
When I had to leave, they threw a party for me, got me very drunk (buying me free drinks, I’d just turned 18) and then put me in a taxi to my brothers house, and let my parents know where I was. 
Working at a movie theater in high school. Little stress, all the free movies you care to see, free food, free drinks.
Ok so cleaning up after a show wasn’t that great but trying to hit the trash can from one end of the theater with a half full cup of coke was a blast!
This is my 1st post so this thread is as good as any to make it on.
My most enjoyable job was during the summer of 1977. I was a U.S. Navy Hospital Corpsman serving with the U.S. Marines at Camp Lejeune, North Carolina. I received orders for “medical duties only” and was sent to the civilian beach attachment on base to render first-aid as needed. My office was in the pavilion right on the Atlantic Ocean shore and served as my home also complete with kitchenette for that summer. I was issued a couple pairs of swim trunks and t-shirts identifying me as the beach “Doc”. I didn’t wear a uniform all that summer, got to grow my hair longer than what regulations allowed and have yet to get a tan as good as I had that summer. I was on the beach from sunup to sundown. I didn’t report to anyone and I had no military formations to stand as I was the only sailor there. For all practical purposes I was on a three month vacation with pay away from the military. At nights I would listen to the roar of the surf and breaking waves as I drifted off to sleep.
Oh yeah, did I mention that I was single then and most of the beach goers were women whose husbands were away on a cruise. I was a perfect gentleman though and didn’t take advantage of the situation. 
– weborator
I currently work as a bike messenger. It’s as close as I can imagine getting to a job that I’d do solely for the fun of it if I could afford to. Also, I think it’s the only job that actually keeps me awake in the mornings. Hopefully, I never figure out how to fall asleep while riding a bike.
My job now, at a university. Beautiful green campus, good boss, light workload, high pay and surrounded by hundreds and hundreds of nubile young students.
And today - they’re all out sunbathing on the grass outside my window.
The only thing that could be better is if I didn’t actually have to be in the office!!
My current one.
I work as a graphics/technical assistant to the art director of a national jazz magazine. I have my own office, a wonderfully powerful G4 with a T1 internet connection, scanner, color printer, and a CD burner. I technically work 9-6, but I’m pretty much free to come and go when I need to, as long as I work 40 hrs. a week and get everything done. I can goof of on the SDMB whenever I feel like it, and play whatever music I want. And the pay is absurd for the amount of work I do.
I also really enjoyed working at a bookstore. A generally intelligent group of employees, at least some of the customers knew how to read, and it was easy.
My current job. The work is interesting, and I like my co-workers.
Owner/operator delivery courier. Hard work, long hours, dodging traffic but I made bank money, was essentially my own boss and got paid to drive all over the Pacific NW, how cool is that? Too bad rising costs drove me out of the business.
during summers at college, i worked as a head waiter in a resturant/night club. my job was to show up (hungover no doubt) at 3pm, set up the room and salad bar, take a break, serve dinner till 10, make sure my minions cleaned up by 11pm. then i was off and partied all night (free drinks!) till about 3-4 am.
the job i have now is cool, but i would rather be home with the kid…