The caboose grew out of an improvised solution to a pressing need in the early days of the railway. Train engines were too crowded for conductors to be able to work comfortably, and with freight trains picking up and dropping off valuable cargo throughout their lines, there was a lot to keep track of. To have a usable workspace, conductors set up offices in older cars. Eventually, these evolved into the caboose as we know it, which functioned not only as a workspace but as living quarters and a lookout post for the crew.

The latter function was vital to a properly functioning train. Conductors needed to be able to see that everything on the train was working properly. If anything broke down, or if the train needed to come to a stop, the conductor would crawl into the top level of the caboose, the cupola, and supervise as crews manually applied the brakes to each train car.

A final use for cabooses was advertising. They have a reputation for being bright red cars at the end of a train, typically painted this color for safety. But cabooses came in many hues — rail companies often painted the caboose to reflect their signature colors and logos, or to match the rest of the train cars.