The Game: GTA III (PS2, PC)
The Level: Grand Theft Auto
The Brick Wall: Delivering three stolen cars in under six minutes sounds easy enough on its face. The rub is that they are located in disparate parts of the city and must be dropped off in perfect condition. Even with the Pay N Spray next to the drop point, the time limit is unforgiving. Definitely took the fun out of the titular felony.
Stuck-o-meter: Low; GTA III practically invented sandbox-style play. It’s a big sandbox, so finding new toys is easy.

The Game: GTA: Vice City (PS2, Xbox, PC)
The Level: Demolition Man
The Brick Wall: You have seven minutes to blow up a high rise by planting bombs with an RC helicopter. The volatile helicopter can be detonated by a light breeze, and there are tons of tight spaces and construction workers with wrenches to contend with. 
Stuck-o-meter: Medium; the helicopter controls are brand new and take some time to master.

The Game: GTA San Andreas (PS2, Xbox, PC)
The Level: Turf wars
The Brick Wall: The game introduces the rules and totally encourages you to begin, but takes away all your progress when you leave Los Santos and forces you to do it over again at the end of the game. You must “take back the hood” by slaying wave after wave of rival gangbangers.
Stuck-o-meter: Medium; this design flaw doesn’t cause too much heartache, unless you spent hours on it the first time through.