In 1867, John O'Hanlan (Stewart) and Harley Sullivan (Fonda) are aging cowboys working on open cattle ranges in Texas. O'Hanlan gets a letter from an attorney in Cheyenne, Wyoming, that his disreputable and now deceased brother, DJ, left him something called The Cheyenne Social Club in his will.
After they make the 1,000 mile (1,600 km) trek to Cheyenne, O'Hanlan and Sullivan learn that The Cheyenne Social Club is a high-class brothel next to the railroad. O'Hanlan's new-found status as a man of property makes him the most popular man in town, until he decides to turn the Club into a respectable boarding house.
The ladies of the Club show no sign of leaving. John gets into a bar-room brawl with several men who are equally angry at the prospect of the Club closing. John then learns from DJ's lawyer that DJ had made a deal with the railroad: if the ladies leave the Club, the land the Club is on will revert to the railroad.
John returns to the Club to discover that Jenny, the head girl (Jones), has been assaulted by a man named Corey Bannister. John, with Harley following along, arms himself and goes to the bar where Bannister is. John kills Bannister when Bannister mistakes Harley's cracking pecans for a second gun. "Just like DJ would have done" the barkeeper intones of John's heroics.
The Sheriff advises John and Harley that Bannister's relatives are sure to head for Cheyenne once they learn of Bannister's death. He says he would like to stay and help John and Harley face down the Bannisters, but has to leave town on business.
Harley heeds the Sheriff's warning and leaves for Texas in spite of John's pleas to stay. En route, Harley meets several men at a campfire. While engaging in conversation with the men, Harley discovers they are the Bannisters. He mounts his horse and rides on.
The Bannisters show up at the Club and a gunfight ensues. John, with help from Jenny, kills two Bannisters from the window. A third Bannister enters the house through a back door and is killed by Jenny. Harley, who has returned, kills the fourth Bannister after climbing the railroad water tower. John yells, "Is that you Harley?" The head Bannister hears this and remembers Harley as the man who approached them at the campfire. He shoots at Harley, but is gunned down by John. The sixth Bannister runs away.
John and Harley are feted at the bar which had formerly shunned them. The Sheriff congratulates them and then tells them 20 to 30 of the Bannisters cousins, the Markstones, are heading to Cheyenne. He says he would like to stay and help John and Harley face the Markstones, but has to leave town again on business.
This time, John decides to leave and he has DJ's lawyer transfer ownership of the Club to Jenny. Months later, while working cattle on the range in Texas, John receives a letter from Jenny. He is touched by it, but tosses it into the fire before him. Harley is upset John has destroyed the letter because he wanted to read it. They then ride off together, arguing.
Set in a brothel with suggestive dialogue, the movie was one of the few off-color films that James Stewart did. He also specifically asked that his friend Fonda be cast; they had most recently worked together two years previously in Firecreek. Stewart and Fonda's first film together had been the musical comedy On Our Merry Way (1948), and they had also both appeared in How the West Was Won (1962) but had no scenes together despite playing best friends.
The exteriors were shot at two Western film lots Bonanza Creek Ranch and Eaves Movie Ranch outside Santa Fe, New Mexico, while the interiors were shot at the Samuel Goldwyn Studios in Hollywood.
The Cheyenne Social Club turned a small profit, and was poorly received by critics. It didn't receive any notoriety until decades later with numerous cable television broadcasts. Barrett's script earned a 1970 Writers Guild of America nomination for "Best Comedy Written Directly for the Screen", but lost to Neil Simon for The Out-of-Towners.James Stewart as John O'Hanlan
Henry Fonda as Harley Sullivan
Shirley Jones as Jenny
Sue Ane Langdon as Opal Ann
Elaine Devry as Pauline
Jackie Russell as Carrie Virginia
Jackie Joseph as Annie Jo
Sharon DeBord as Sara Jean
Robert Middleton as Barkeep
Robert J. Wilke as Corey Bannister
Dabbs Greer as Jedediah W. Willowby