The Culpepper Cattle Co.

Teenager Ben Mockridge feels life in a Wild West farm town has nothing better to offer than horse-cart racing with other hicks, so he naively begs cattle company owner Frank Culpepper to engage him as the youngest cowboy for a long cattle trail to a fort. His mother barely notices. Ben doesn't even seem to get it when he's told to report as 'little Mary' to the old cook, whose words, "Cowboy is something you do only if you have nothing better." gradually become clear. Instead of an exciting heroic macho life, it's endless hard work, dumb chores and embarrassment, even getting literally caught with his pants down, robbed of his horse, and witnessing unpunished crimes... - IMDb