That sounds awesome!
Security guard for a very strange office building. Our office was in the basement, we had 2 officers per shift, and all that we did was patrol building one person every other hour, and watch monitor. Oh, and answer the phone. We could read, blab, radio, etc… Oh, and smoke cigarettes non-stop. We all smoked! This was 1997-98, so we realized that the times were special. We were all a bunch of crackpots, and IIRC, we all believed in UFO’s, or at least some serious government conspiracies. Some great people, not what I consider the norm for security guards: We were all looking forward to better times, and not bitter about being there. We had a tight little group. I had sex OTJ with one of the female officers, another became a very dear lifelong friend, and, we all, on changing shifts, sometimes even had group hugs. Cornball, but we all liked each other. I was sorry when it ended.
Lifeguard at a waterslide.
Have you considered pitching this as a screwball comedy?
Summer camp counselor. I loved that job.
It was like being paid (a very paltry amount) to go to summer camp and goof around and flirt with boys. And even with all that, I was a good counselor and very responsible with the little kids.
I worked retail for $4.25/hr when I was 16 (that was the minimum wage). It probably wouldn’t have been as fun if I wasn’t working with a bunch of other teenagers, with some older pothead teenagers running the stock room, and some managers who clearly were too immature to get along in a more important job…but I totally look back fondly on that time.
I’ve had other, more fun jobs but they paid double that or more.
I don’t know, I liked the job at the cabinet factory because I had my own mini-empire with a bunch of cool people. I liked working at Pizza Hut because the waitresses were hot and drama queens, the drivers were awesome and my manager was like another mom to me. We used to stay up until 2 AM drinking and playing dime poker in the dining room sometimes.
I think my favorite job though was working at a DSL company in the tech support area. I got to talk to all kinds of interesting and hilariously dense people, my coworkers and I were all practical jokers, and when I moved to the Abuse team, I got to shut off people’s internets :D. I’d still be doing it today too if they hadn’t closed up all of a sudden with an hour’s notice right before Christmas.
DJ at a college radio station. Paid nothing as it was volunteer. I ran the station for a year on a $300/month stipend. Best.fucking.job.I.have.ever.had.
When I was young n’ hot and had long blond hair I could sit on, I sold tickets and sometimes worked the snack bar (hair under restraint, of course) at various movie theaters. That was FUN. Free popcorn, soda, and movies, made great friends that I worked with, got a couple boyfriends out of the deal.
I worked for a non-profit in social services capacity, secretary to several social workers. We formed a very close bond, very much like a family. (There were other departments in this non-profit and since we dealt with street people, we were looked upon as ‘flakes’ by the humorless stick-up-the-ass accountants and medical people who had cleaner jobs.) I made very little, but it was a long time ago when things didn’t cost so much. One of the social workers had a relative who rented me a flat for $135 a month, I had a car I made reasonable car payments on, and I spent the rest on clothes and shoes! Plus we had a lot of free meals and outings through work.
I spent 6 years working in a Pet Store. Basically cleaning up sht for a living. Aside from dealing with the sometimes incredibly ignorant general public, I loved every minute. We became like a family and hung out and laughed all the time. I don’t miss the lousy pay, no recognition or appreciation from the boss, did I mention the cleaning up sht part? But I do miss getting paid to walk around with a parrot on my shoulder all day.
Hands Down…EMT-1 Ambulance on weekends.
No management around so it made it easy.
At the time I was making $5/hr (min wage was 4.25) but we usually worked 50-60 hours a week. The vast majority of the time we were screwing around, watching TV, whatever.
Most weekends we would BBQ at the station, play laser tag, sometimes we would all go out to the movies at the cheap theatre and if we got a call, we left. 60% or so of the time we did not get a call.
Of course when we did get a call, it was all nose to grindstone, and as always rarely boring or uninteresting. Every call is different, so its always a little adventure.
Next best:
Self employed computer shop owner
The money is still not where I would like it to be but man its got alot of the EMT job in it as far as the always different, always changing.
Organizing political campaigns.
I worked retail in a book store. I met a lot of fun people (and a few celebrities), loved helping people find JUST the right book, sometimes with very few clues, but the pay was crap.
I’ve had a few, mostly before I went to college.
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In Indonesia, I was a DJ with my own radio show on one of the main radio stations (Radio Darmawangsa). Got to choose the music I wanted to play, recorded the intro to the song and a little bit of chatter. The whole purpose was to give Indonesians a chance to listen to English phrases in a realistic setting. Great stuff for a 15-year-old. The pay? Absolutely nothing, but was a great 6 months.
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Also in Indonesia, I had a summer job working on an oil rig as a radio operator. Duties included sending in daily reports via radio, plus handling chopper and boat traffic. Worked 12 hours on, 12 hours off, for 14 days straight, then off for a week back on shore. The pay was $1.50 an hour (this was back in the summer of 1979). Plus, all the food I could eat, and then some. For entertainment, we played a lot of pool, and I got to be pretty good. Not to mention the very interesting magazines and videos which were stockpiled on the oil rigs.
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Straight out of high school (summer of 1980), I got a job in Hawaii as a surveyor’s assistant doing topographical surveys. (Orange vest, surveying instruments, that sort of thing.) Highlights included surveying some really wild territory out by the Polynesian Cultural Center where there were herds of wild cows and horses. I helped discover some ancient Hawaiian site. We also got to survey parts of Waikiki Beach, and I had to swim out into the ocean to measure the ocean floor for a drainage project. I think the pay was somewhere around $5-7 per hour.
Great times, great times!
In college, I worked in Master Control for a TV station. I’d come in for my six hour shift, make sure the system was set up right for the evening and then keep half an eye on the monitor while I watched other satellite channels or videos on the preview monitors, ordered pizzas, called friends and my girlfriend at the time would visit and we’d have sex in the control booth. It was about 5-10 minutes worth of work for a six hour shift with the rest of the time spend screwing around.
I was making barely over minimum wage for it but was probably overpaid.
Nanny! Although, I do get to go to Argentina this month with the fam.
Actor, and while Shakespeare was very fun, the most fun was the disturbingly good pirate show we did at a tiny rennaisance weekend in Georgia. The choreographed bar-brawl was a thing of beauty, and while we lost money on the whole thing due to hellish technical difficulties on the way back, it’s an experience I’ll never forget.
Writing for an RPG that I love. When the question came down, “Hey, would you like to write for the next sourcebook?” I was high as a kite just off the offer. The money wasn’t great, but having the bragging rights is pretty nice.
Getting money from payphones. I drove around Chicago with the owner of said phones, and we’d munch fried chicken and listen to the radio. Stop a few dozen times, load bags with quarters, drop it all off at the bank, then head home. It was really relaxing.
I spent a summer [url="http://www.rollingthunderriverco.com/Nantahala-River-Rafting-Information.cfm"guiding rafts for an outfit in North Carolina. The pay was shitty, the hours were brutal, the work was hard, and the summer crew lived in shacks.
I loved every minute of it. I’d do it again in a heartbeat.
And a second for delivering pizza. Yeah, it could kick my ass some nights, but I made a ton of money and had a lot of interesting 
experiences.
Independent Record Store in the middle of the nineties alternative rock boom. It was everything that movies like High Fidelity and Empire Records made it out to be, and more. Weed in the bathroom, sex in the stockroom, sleeping in the store, massive theft and embezzlement, an independently wealthy cokehead owner who lived hundreds of miles away and dropped in once every six months, etc.
Time of my life. 
Bookstore clerk, back in High School. I got an employee discount, and ended up spending my whole paycheck on books.