The origins of both the car and the word are surrounded as much by legend as by fact. One popular version dates the word back to a derivation of the Dutch word "kombuis," which referred to a ship's galley. Use of cabooses began in the 1830s, when railroads housed trainmen in shanties built onto boxcars or flatcars.

The caboose served several functions, one of which was as an office for the conductor. A printed "waybill" followed every freight car from its origin to destination, and the conductor kept the paperwork in the caboose.

The caboose also carried a brakeman and a flagman. In the days before automatic air brakes, the engineer signaled the caboose with his whistle when he wanted to slow down or stop. The brakeman then would climb out and make his way forward, twisting the brakewheels atop the cars with a stout club.

Another brakeman riding the engine would work his way toward the rear. Once the train was stopped, the flagman would descend from the caboose and walk back to a safe distance with lanterns, flags and other warning devices to stop any approaching trains.

Once under way, the trainmen would sit up in the cupola and watch for smoke or other signs of trouble from overheated wheel journals (called hotboxes).

The addition of the cupola – the lookout post atop the car – is attributed to a conductor who discovered in 1863 that he could see his train much better if he sat atop boxes and peered through the hole in the roof of his boxcar.