Teenager Ben Mockridge feels life in a Wild West farm town has nothing better to offer then horse-cart racing with other hicks, so he naively begs cattle company owner Frank Culpepper to engage him as 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, witnessing unpunished crimes…

Jeff Bridges stars as young con man named Jake Rumsey in this highly original Western. After Drew Dixon (Barry Brown), an upright young man, is sent west by his religious family to avoid being drafted into the Civil War, he drifts across the land with a loose confederation of young vagrants.