City Slickers (1991)

Mitch is a middle-aged big-city radio-ads salesman. He and his friends Ed and Phil are having mid-life crises. They decide that the best birthday gift is to go on a two-week holiday in the Wild West, driving cattle from New Mexico to Colorado. There they meet cowboy Curly who not only teaches them how to become real cowboys, but also one or two other things about life in the open air of the west.