This is the #P41 Black Pinto Prancer with Indian. (See record #P41 for model details). Set #P241 'Indian & Pinto' came with Indian Rider, tomahawk, knife, and 4 arrows with metal bow and plastic quiver, fabric bareback blanket with elastic band cinch and chain reins. Blankets were typically red, but came in several patterns and accessories came in different colors such as red, yellow and clear copper (as shown in photos). Production dates are estimated 1954-1957. The Western Pony is estimated to have been released in 1953, or earlier, but the Prancer is pictured on the boxes; therefore, it is just assumed that maybe the Prancer could have been released in 1954 (or maybe earlier). The Indian and Prancer were not pictured in the catalogs.
Early versions of the Indian have buckskin colored pants and moccasins with a red loincloth, red headband, and warpaint on the chest, face and arms. Originally released with only a feather that fit into a hole on the right side of the head. A paper headdress was released shortly after, and then the plastic headdress. Later versions of the Indian have turquoise pants and moccasins, light tan loincloth, a turquoise headband, and warpaint on only the chest and face. Most Indian molds have black painted on eyes, eyebrows, and red lips, though it's possible some models did not have painted faces. See photos of the painted variations. The Indian mold was sculpted by Chris Hess, and has no mold marks or Copyright Stamps.
Sears: 1955-1956 as 'Musical Indian-On-Horse'. Included Indian figure with removable paper or plastic headdress, arrows, tomahawk and knife and a music box key. Music box parts are Swiss made. Original price $5.98. Song is "From the Land of Sky-Blue Water", by Charles Wakefield Cadman. (YouTube: https://youtu.be/q-ki-Y2ubgQ). Most Music Box models have 2 visible screws; however, the earliest models only had the one wind up screw. The second one was needed to help secure the box inside the horse. The 1955 Sears ad shows the Indian with the buckskin pants and warpaint on the arms (similar to #241 Western Pony set) and paper headdress, and the 1956 Sears ad looks like it could be the turquoise pants version, with no warpaint on the arms and a plastic headdress. See photos of the painted variations.
Pictured: "This is a rare Glossy Black and White Pinto Prancer Music Box complete with Indian Chief, all accessories including the incredibly rare paper headdress and metal bow, and the original instructions. The back of the set shows off the accessories: knife, tomahawk, bow, quiver, and arrows. The accessories were made in a variety of colors such as yellow, red, white, brown, and even translucent red." - Kirsten Wellman.