What made City Slickers a hit?: The Western was one of classical Hollywood’s most popular genres. But while the greatest Westerns have endured in the American consciousness to this day, the popularity of Western films went downhill during the 1960s. By the 1980s, the number of Westerns made by Hollywood had dwindled to a handful of titles per year, and only a few of these (Young Guns, Dances With Wolves) made any money. At a time when people sat through long commutes to work and sweated the economic recession, it was hard for most audiences to relate to the old-fashioned cowboy mythos.
Yet even then, Westerns exerted a pull on our imaginations. The inspiration behind City Slickers was the way it combined the pleasures of an old-fashioned cattle-drive Western with characters with whom the audience could identify. The movie’s heroes weren’t larger than life, but rather a trio of middle-aged everyguys trying to escape the doldrums of modern life- bad marriages, dead-end jobs, fears of growing old- by embracing (after a fashion) the cowboy lifestyle, if only for two weeks. Add to this the presence of popular comic Billy Crystal, who has recently shown his leading-man chops with 1989’s When Harry Met Sally, and the combination of comedy and cowboys proved irresistible to audiences. City Slickers became one of 1991’s biggest hits, raking in nearly $125 million at the domestic box office.
What happened?: Sometimes, there’s no easily-pinpointed factor to explain a movie’s fall from its original level of popularity. While some blockbusters continue to factor prominently in popular culture and others fall from grace, most just sort of fade into the background. Of course, the misbegotten 1994 sequel City Slickers II: The Legend of Curly’s Gold didn’t help matters. But mostly, City Slickers’ lack of enduring pop culture influence can be chalked up to the fact that it appealed primarily to middle-aged moviegoers, rarely the sort of audiences that fanatically obsess over a movie until it enters the popular lexicon.
Does City Slickers still work?: It mostly does, although it’s not without its drawbacks. For a movie that was sold primarily on its famously funny leading man, the comedic scenes are among the movie’s least effective. Part of the problem is Crystal, whose trademark kvetching (and oft-repeated refrain of “hel-loooooooooo???”) quickly becomes irritating. Not helping matters is director Ron Underwood’s misguided decision to underscore all of the big slapstick moments with jaunty, cutesy music by Marc Shaiman. These scenes lean too heavily on the wacky factor, which drains away whatever wit was originally there.
But while it’s not nearly as funny as it thinks it is, City Slickers is a sturdy and self-aware twist on the Western genre. Despite their fast-paced modern lives, lifelong friends Mitch (Crystal), Phil (Daniel Stern) and Ed (Bruno Kirby) were raised on Westerns, and this colors their experiences on the trail. They show both fear and respect for aging trail boss Curly (Oscar-winner Jack Palance), who Mitch proclaims “the toughest guy I’ve ever seen,” but the two of them also bond during their time together on the trail. The characters explicitly reference Red River, The Magnificent Seven, Rawhide, Bonanza, and other favorites, but they do so in a way that presents them as shared pieces of their past instead of simply clever allusions. And the movie becomes surprisingly exciting when the unlikely cowpokes have to bring the herd in by themselves, and it’s a satisfying scene when they actually pull it off.
However, City Slickers is at its best when dealing with the friendship between its heroes. Screenwriters Lowell Ganz and Babaloo Mandel were Hollywood’s go-to guys 
in the late eighties and early nineties for mainstream fare about middle-aged everyguys, and this movie demonstrates why. Likewise, Crystal, Stern and Kirby have an easy and infectious bonhomie that makes them convincing as three men who’ve remained friends through both good and bad. The late Kirby is especially good as the most pragmatic of the three, who worked his way up from a difficult childhood to create a comfortable life, but has never lost his taste for adventure. And verbal shtick aside, Crystal is affecting as the ill-at-ease salaryman Mitch, who ventures West with his lifelong friends with the goal of “finding his smile.” In the end, he does, and so did I.