Interesting topic. Here's some thoughts:
1) Like NW-Bound, I've always said that if the job were truly fun, they could get volunteers to do it. (Note, there are a lot of volunteers working in national parks.)
The exceptions seem to be where the job requirements are so extreme that only a limited number of people can do it. (Lots of people would volunteer to play the Masters, but only a handful clear the entry requirement of having a realistic chance of playing the 72 holes at par.)
2) The book of Genesis has a good insight. Most work isn't inherently unpleasant. Adam had a job (he was the gardener) but he lived in paradise and enjoyed it. When he got kicked out, he still farmed, but suddenly he had to contend with "thorns and thistles". In a lot of jobs, the "gotcha" is other people who don't deliver when promised, or do expect the impossible, etc. I always figured they were the thorns and thistles in cubicle life.
3) Early in my career I went to an inhouse course on "career management". We did an exercise where we listed a couple dream jobs. Then, at the next session we filled out a priority list on characteristics of good jobs (time with family, high income, independence, security, travel, etc). It turned out that most people discovered their dream jobs didn't line up very well with some critical priorities. I was an exception, probably because I'm so analytical that I'd instinctively done this exercise before I picked a career.
All that aside, my personal dream jobs are: Pro Golfer (if I didn't have kids) or Philosophy Professor at a liberal arts college.
Both have high bars for admission. Nowadays, the gotcha for both could be PR work.
