Using the SkateboardEdit
Although it is a vehicle rather than a weapon, Jimmy carries it at all times, and must equip it to use. PC version of Scholarship Edition has an external button allowing Jimmy to quickly equip / unequip the Skateboard instead of having to scroll through the Inventory Wheel. In the PS2 edition by hitting L2 and R2 together it can be equipped and on Wii you can press both + and - buttons at the same time. It is slower than a bicycle but faster than walking on foot. The skateboard accelerates when going down hill, and decelerates while going uphill. Snow on the roads gives the skateboard less traction and makes it harder to steer. The skateboard is very slow on grass and dirt and won't gain momentum. Jimmy can do ollies on the skateboard simply by pressing the O button on the PS2 version and down on the Wii while at speed. By pressing the Triangle button near the rear of a moving car on the PS2 edition of the game, Jimmy can skitch a ride. Skitching allows the player to have a free automatic ride, however the downsides are that it raises your trouble meter a bit, and you cannot control where the car you have latched on to will go.
Riding the skateboard inside the main building is "Misconduct". While riding it, Jimmy's Trouble Meter fills slowly, although never past pale yellow. However, this will not take place when he is going for his Class, before the truancy meter starts to fill.
Riding the skateboard also makes Jimmy immune to taking damage from falling. He can jump off the tallest buildings while riding the skateboard with no ill effects. However, if Jimmy attempts to ride up stairs or runs into a wall using the skateboard, he will crash and take minor damage.