City Slickers

City Slickers (1991) is a comedy Western with Billy Crystal you can watch online on iFILM. Mitch Robbins is about to turn forty, his job bores him, and nothing feels like fun anymore. So for his birthday his friends sign him up for a two-week cattle drive across the open range.

Three New York buddies — anxious Phil and skirt-chasing Ed alongside Mitch — climb onto horses they've never ridden, herding cattle they know nothing about. Running the drive is Curly, a leathery trail boss carved out of granite; Jack Palance plays him and walked away with an Oscar for it. Expect dust, blisters, ridiculous arguments, and one newborn calf named Norman that Mitch quietly falls for. The vacation that was supposed to fix a midlife slump turns into a real test of nerve.

Director Ron Underwood pulls off the rare trick of a comedy that's both genuinely funny and warm without going soft. Crystal carries it, but keep an eye out for a very young Jake Gyllenhaal in a small early role. Stream City Slickers (1991) online on iFILM.