I'd want to be Maat from Final Fantasy XI.
He's the guy you have to do the most annoying tasks to increase your level cap from level 50 to 55, 55 to 60, 60 to 65, 65 to 70, and 70 to 75.
The first time around, you have to collect ancient papyrus, a bomb core, and exoray mold from some of the harder monsters in the game, each with a drop rate of like 1%, oftentimes taking almost forever to do.
The second time you have to kill three monsters and get an item from behind them. These guys aren't hard, but it's still annoying to have to do.
The third time you have to go around collecting seals from the absolute depths of three Beastmens' major living areas, always having to open hard-to-open doors and having to pass through monsters that can see you and will attack you on sight even with Sneak and Invisible on.
The fourth time you have to go around talking to various NPCs throughout the game, trivially taking up time.
The fifth and final time, you actually have to fight him. As some jobs, he's easy. As other jobs he's nearly impossible. As a few jobs actually, it's a real gamble. The guy's like 80 years old, he always uses his fists to fight, and he can punch your nose through your skull in five seconds if you let him. Best of all, he never dies. He 'gives up' at 15% health, so he can never die. You would always win. If you beat the adventurer, you get to say "I'm an 80-year-old man and I just beat up a 20-some-year-old adventurer," and if you lose, you can still say "I did a damn good job for an 80-year-old man. Damn whippernsappers."