Putting money aside from the discussion, and just going with jobs I enjoyed...
Managing an arcade back in the 80s. Loved the games and pinball, and although keeping the machines running and assorted hassles was a pain, I loved the environment.
Went from the arcade to managing a deli in a college town. Super chill, employees were great. We were open super late, lots of college girls; it was a good time.
Startup I worked for. Busted ass there, we all did, but I've never worked with a more eclectic group of people. Almost everyone there was like an expert in something else other than the software we were working on. Just a fascinating group to hang with every day, and really enjoyed that place. All good things come to an end though.
I've had a good time at some other jobs, and don't hate my current gig at all, but the above were fond memories.