Pain allows players to put a character into an urban environment to create as much chaos as possible. Launched from a human-sized slingshot, the player's character needs to complete specific goals or inflict as much damage as possible by stringing together painful collisions. The gameplay is similar to Truck Dismount and Stair Dismount, where players can steer their ragdoll through the environment, known as Ooch in the game. The game's environment is set in a downtown area and offers six different game modes with the initial release.
The single-player modes include Mime Toss, where players grab a mime in mid-air and hurl it through panes, and Paindemonium, which features sandbox gameplay. Multi-player modes offer Bowling, where up to four players bowl themselves while others throw mimes, anvils, explosives, or cereal in their path.
Other multi-player modes include Fun With Explosives, where players target crates to cause big explosions, and HORSE, where players take turns launching powerful shots to cause maximum damage. By doing well, trophies can be unlocked in the trophy room.