I've worked at, in order:
---High School---
Pizza Hut as a waiter. Sucked.
McDonalds as a cashier. Sucked. They stopped putting me on the schedule for two months straight, so...
Wendy's. Sucked. Got a call three months in telling me I was fired from McDonalds because I hadn't shown up. WTF? I hadn't worked there for five months. Apparently I was supposed to come in every week and look at my schedule, even though they stopped putting me on it. In the mean time, I was supposed to do what, exactly, about my car insurance and gas bills? Bastards.
---College---
Sonic. Amazing job. Manager would come back and help out during the rush. 100% of the pay was mine to keep. No stress, no bills, no real responsibility. Sadly, it interfered with my class schedule.
Work-study (graphic arts dept). Boring. Helped out maybe two people during the year I was there. Taught one class how binary worked. Cool teacher, though.
Work-study (IT Helpdesk). Not a bad job. Kept me busy, learned a lot, had a boss who took my side against a higher up.
Internship (Northrop-Grumman certification and accreditation). Worst job in my mind. Best paying so far, but holy cow was it dull. Sit alone in a room for 8 hours writing paperwork you don't understand about a system you're not allowed to see. Still, because of this internship, I landed:
---Real World, take 1---
3D Graphic Artist (Northrop-Grumman). I got paid more than my previous job, to create video games. It was my first real "professional" job, and the group was full of whacky people. Everyone was excited and enthusiastic. Everyone was friendly. There were a lot of people my age around. They paid for my security clearance. I rented an apartment and bought a Miata, my first new car. Then my boss's boss went and committed corporate espionage. Northrop gave me two months to find another job while I looked for security vulnerabilities in EFI code. Didn't find one. Dream over.
---The contract years---
After six months of looking for a job, I finally got in with a headhunter. They landed me a 6-month contract with Lockheed-Martin as a Solaris Systems Administrator. It was my first graveyard position, but the salary was better than any I've ever had before, and the job was something I was interested in. The people there were good folk. Not as enthusiastic as my previous job, but knowledgeable and friendly. It paid off my credit card debt. Then I made a series of mistakes that got me let go. Decided to go back to school.
After finishing up my Bachelor's degree, the same headhunter had me working for the county as a Windows/Linux SysAdmin. Pay raise, but it wasn't worth it. Dreadful place. No smiles, no fun, all business. Grumps abound. Worked there for a year and a half (I think), before getting into a yelling match with a coworker that resulted in me being let go again. I was honestly relieved.
Two weeks after that, I was in a job at JDSU. Linux SysAdmin. Learned more here than at any previous job. Nothing really exciting, just 8 hours a day of simple work. I watched the industry average pay for my position continue to rise, and watched my pay continue to stagnate. When my contract ended, they asked me if I wanted to continue working for them. I told them "Yes, but I've got to have a pay raise. I'm 30-40% underpaid depending on who you talk to." They hemmed and hawed. During this time, I went looking for non-contract work. Found it, at a pay raise, plus some damned good benefits. JDSU gave me a 15% raise. I handed in my two week's notice.
---Modern day---
I started working at my current company as a night shift guy. Between the shift differential and a little bit of overtime, I'm making literally twice what I was at JDSU. Plus I've got health care, retirement benefits, actual training, etc. I'm only six months in, but I love the company. I can't see myself in this job 10 years from now, but I can definitely see myself with the company. This is my first time as an application guy. Normally I'm more infrastructure. As for the job itself? A little dull, to be honest. That's okay, though. It's nice, lazy, brain work. It allows for time to self-improvement. Hell, the company will pay for my Masters, which I'm thinking hard about. My coworkers aren't the young, enthusiastic folk they were at Northrop, but they've got skills I can only dream about. I figure, a couple more years to really learn the applications, then I'll slide over to networking or go for a management track.
So, best job I ever had? That's a tough one. It's either a tossup between the carefree Sonic days of a teenager, or the passionate days as an artist with Northrop-Grumman.