An advertising system and method of use includes a rail car and an advertising billboard mounted thereon. Preferably, the billboard is adjustable so that advertising thereon can be positioned to face desired viewers, such as people traveling on roadways adjacent a railroad track. The billboard may rotate and/or be raised and lowered by a lift, which may include a telescoping post. An onboard electric power source is typically provided to power lights and other electric components. Outriggers may be used to help stabilize the rail car when parked especially for windy conditions. A security fence may be mounted on the rail car to protect various components thereon. The billboard may include one section which can be raised relative to another section for display purposes and lowered to provide a lower height during transport. The rail car may carry an additional billboard.