Bob the Robber is a puzzle platformer with dungeon crawl elements similar to Money Movers. Ever since Bob was a baby, he admired Robin Hood and the idea of stealing from the rich to give to the poor. During his childhood, he often practiced burglary and lock-picking skills to guarantee that he would become the greatest thief ever. With a feather in his cap, he's ready to take on the biggest and wealthiest crooks in the city. He just needs the player's help on his crusade!
The player guides Bob through his training warehouse, a jewelry store, a mansion, a bar and a casino. The goal is to steal from publicly respected criminals without getting caught by guards or security cameras. The player must direct Bob to be as sneaky as possible while moving through multiple levels of a building. They must also help him read notes on walls, pick manual locks, find and use electronic lock keypad codes, hide from or disable security cameras, turn off red laser barriers, and attack anyone or anything in his way.
Bob the Robber offers several methods for earning money and points. The player can discover hidden valuables by searching boxes, furniture and other objects. They also earn bonus points for moving through a building quickly, collecting a certain amount of cash, and not setting off any alarms. The game rewards up to five stars per building as well.