When most of us were growing up watching trains, it was always special to see the caboose at the end, and maybe get a wave from one of the men riding it.  The old railroad saying was "a train is not a train until the caboose is hitched and the markers are hung".  Today with some exceptions, the caboose is a thing of the past.  With the modern diesels, the entire crew rides up in the cab, and electronic devices (FRED) monitor the status of the train.  Riding the caboose was not the safest job on a railroad, but it is large part of the romantic past.
    There were many different types of cabooses used by the railroads.  Many were built in each railroad's own shops, though ACF and others were often contracted to build cabooses to a particular railroad's specifications.   These cabooses came in many different configurations.  At the beginning, cabooses were modified box cars which rode hard, were hot in the summer, and cold in the winter.  Eventually the railroads got smart, and began thinking about crew comfort and safety.  Steel under frames were added for collision protection and to eliminate having to uncouple the caboose when using helper locomotives. Electric power was provided for lighting, and in some areas, air conditioning was added. 
    Fortunately for us in large scale, we have a fairly nice selection of caboose models to choose from for our miniature railroads.  As I go through my little historical tour, I will mention various models that are available.  I may not list every type available, but will try to cover as many as I can.
    The earliest cabooses were not much more than boxes on wheels. The first that were built new were often small and rode on four rigid-mounted wheels. They acquired the term "bobber" because of the rough ride they gave the train crews. Many were built of wood, but some steel bobbers were built.  Aristocraft makes a bobber caboose (1/29), along with LGB(1/22.5) who has several with centered and offset cupola, and of course Accucraft (1/20.3) with its Western narrow gauge flavor, has a couple that are offered to the modeler, along with a special bobber for the Westside Lumber Company. These cabooses will fit well in railroads that are themed for either narrow gauge or mainline pre-1900's.
    The cupola ( pronounced kyoo pa la) caboose is the most common caboose found on railroads over the past century.  This innovation gained widespread acceptance because it provided a "crows nest"  for the train crews to watch over their trains.  The cupola could be found in many locations on the car. It could be centered, offset, or even at the very end of the car, depending upon the railroad's preference.  In some cases, safety belts were provided for the cupola crew, as a quick start or stop could throw them from their perch and break bones.  These cabooses were also built of wood or steel depending upon the railroad.  Model cupola cabooses are available from several manufacturers.  Aristo (1/29) makes a steel caboose with offset cupola, USA (1/24) makes a wood sided caboose with offset cupola, LGB (1/22.5) makes a steel caboose, which is a model of a steel Santa Fe caboose with offset cupola and also a D&RGW drovers caboose, MTH (1/32) makes a Santa Fe type caboose, and Accucraft (1/20.3) makes a D&RGW long caboose with offset cupola.  LGB (1/22?) also had an cupola caboose, that was a model of a White Pass and Yukon caboose, but it is now out of production.  No manufacturer of large scale equipment as yet, has made the distinctive centered cupola "Northeast" style caboose similar to what the Reading and Lehigh Valley ran.  The last model of this was made by the American Flyer company for its "S" Gauge line. Aristo (1/29) had a limited run of brass Pennsy NC style cabooses, but the run was not large, and the cost was high.
    As trains became taller, due to the introduction of "high cube" boxcars, piggyback trailer loads, and container cars, the cupola caboose started to lose favor.  The railroads could not build the cupola higher to provide vision over these type cars because of tunnel, bridge, and other clearance restrictions especially in the Northeast.  UP made an attempt at making the cupola higher, but this did not totally correct the visibility problem.  As a result, two types of cars emerged from this situation, the bay window and the wide or extended vision cabooses.  The bay window caboose did away with the cupola completely, and substituted protruding bay windows on each side of the car, which allowed trainmen to view the length of the train from safe location.  The wide vision or extended vision caboose, took the cupola and widened it beyond the sides of the car so that the train view could get the same view of a bay window but with the added height of the cupola.  USA (1/29) makes a bay window caboose and also a wide vision caboose in a variety of road names.
    While the models of most of the cabooses listed may not perfect replicas for a particular railroad, modifications, added details, kit bashing, paint, and decals can make your caboose more like the railroad you model.  I have seen many kit bashers who have done an excellent job of changing the appearance of a model caboose to make it more closely resemble the prototype railroad that they model.     
Bay Window Caboose
Wide-Vision Caboose