At the height of his career, Billy Crystal starred in City Slickers (1990), a fish-out-of-water story about three New Yorkers who land on a Southwestern cattle drive by way of a midlife crisis. The smashhit came for Crystal on the heels of When Harry Met Sally (1989), and he had just hosted the first of seven consecutive Academy Awards.
Which is all to say: Crystal was a big star in 1990. He had climbed up from his first bit role (as TV's first gay character, nonetheless) in the '70s sitcom "Soap," through standup clubs and passed through "Saturday Night Live" before landing the brief role as funny leading man. City Slickers was Crystal's zenith, as his career (and jaw line) sagged from there forward—still, not a bad peak to reach.
The film hopscotches around slapstick gags, but it also takes moments to pause and truly examine male struggles with their identities, responsibilities and masculinity—at least with more intelligence than contemporaries like, say, the Hangover trilogy.
It is also one of the best examples of the cowboy comedy, one of the many sub-genres of the age-old cowboy movie.
With cowboy movies often overly stoic (picture: Clint Eastwood unsmiling, unspeaking and squinting in The Good, The Bad and the Ugly) or morally oversimplified (note: any John Wayne movie), they are often the easiest to mock. (City Slickers, for example, is a sly sendup of John Wayne's The Cowboys ).
Of course, Blazing Saddles (1974) is perhaps the consummate Western spoof, managing to lampoon nearly every stereotypical Old West character—like a Yiddish-speaking Indian chief and a drunken gunslinger played by Gene Wilder fresh off his career-defining role as Willy Wonka. Although the film is more often remembered for its quippy one-liners and sendups, it truly holds together as a solid narrative, aptly picking up the common cowboy morality tale that pits hard-working town folks against the deceptive, money-grubbing bureaucrats (and the film was nominated for three Academy Awards, after all).
But perhaps the most genre-bending and greatest cowboy comedy of all time is Butch Cassidy and the Sundance Kid (1969). Although not often remembered as a comedy—and the film does end just that hairline moment before the two anti-heroes are riddled with bullets from the Bolivian army (whoops, spoiler alert)—the movie is hee-hee-larious! Butch (Paul Newman) and Sundance (Robert Redford) bicker throughout the film like the Sunday comics' Lockhorns. Butch simply cannot shut up. He talks a blue streak and constantly chides Sundance with the biting yet good-natured ribbing with which an older brother gives his younger sibling headlocks and noogies. What works best is that Butch and Sundance make the tough-guy genre funny not by using the normal gags, like cowboy-jumps-on-horse-and-crunches-his-nut-sack or forked-tongued Indians, but with nuanced and likeable characters who simply are funny, in spite of being real cowboys. SW