Mitch (Billy Crystal), Phil (Daniel Stern) and Ed (Bruno Kirby) are all undergoing mid-life crises and head to a vacation at a dude ranch in New Mexico. During the cattle drive to Colorado, their trail boss, Curly (Jack Palance), terrifies the trio and the rest of the vacationers into line by wielding a knife with precision, lighting matches by striking them on his own face and stopping a stampede by simply whistling loudly. After the stampede, Curly takes Mitch to gather a few stray cattle and the two become friends. Curly, having seen many tightly-wound city folk come out for vacation, imparts the advice to Mitch that each person needs to find the "one thing" that matters to them the most, then everything else won't mean shit. Mitch helps Curly deliver a calf, that Mitch names Norman, but Curly is forced to shoot the mother cow.
Upon returning to the group, Curly dies of a heart attack. The remainder of the cowboys are all drunks and Mitch, Phil, Ed and the rest of the vacationers are soon left alone with the herd. Ed and Phil attempt to bring in the herd themselves while Mitch and the others leave to find help. As Phil and Ed struggle hopelessly with the cattle, Mitch rides over the hill, wearing Curly's hat, and the three begin to move the herd to Colorado.
While fording a river with the herd, Norman is swept downstream. Mitch rides after him and lassos the calf from horseback, a move he couldn't even attempt a few days earlier, but he is yanked off of his horse and the pair are swept downriver into the rapids. Phil and Ed ride down the riverbank, get ahead of the pair and form a human chain off of a tree trunk that is protruding over the river. Mitch grabs on and he and Norman are saved from drowning.
The trio manage to bring the herd to Colorado, the dude ranch owner Clay (Noble Willingham) refunds their money and informs them that the entire herd is headed for the slaughterhouse. Mitch is upset, but brings Norman home to New York City with him, along with a sunnier disposition towards life. Phil, finds new love with Bonnie (Helen Slater) and Ed resolves to become a family man.
Thanks Evil Ed!