The Cisco Kid (Baxter) is a thief and outlaw in the Arizona Territory in 1898. (Arizona did not become a state until 1912.) He is a rather gentlemanly thief, holding up Wells Fargo stages but refusing to steal from individuals; when the Kid finds out that the town barber lost $87 from a gold box that the Kid robbed, he returns the money.
He is also humanized by his love for a beautiful maiden, Tonia Maria (Dorothy Burgess). The Kid is devoted to Tonia Maria and plans to get out banditry and take her back to his homeland of Portugal. What he doesn't know is that Tonia Maria is actually not in love with him at all, bleeding him for money and presents while also apparently working as a prostitute while he's away. While the kid is off pulling what he imagines will be One Last Job, Tonia Maria falls for Sgt. Mickey Dunn (Edmund Lowe), who is active duty in the local cavalry battalion. Mickey has orders to be transferred back to Governor's Island in New York City, and he promises to take Tonia Maria with him and show her the high life. They hatch a plan, one that involves the $5000 bounty for the capture and killing of the Cisco Kid.
Adapted from the O. Henry short story "The Caballero's Way". In Old Arizona was one of the first all-talking films ever made. Much of it was shot outdoors when most early talkies were indoor pieces with actors standing rooted next to hidden microphones. Warner Baxter won the first Best Actor Oscar for a talking performance for his portrayal of the Cisco Kid.
Director Raoul Walsh, who had both acted and directed his previous feature Sadie Thompson, was supposed to play the Cisco Kid as well as direct. One night while he was out driving around on location, a jackrabbit leaped up and crashed through his windshield. Walsh lost an eye, and wound up being replaced by Baxter in front of the camera and Cummings behind it. Walsh wore an eyepatch for the rest of his life and never acted again, but enjoyed a long and highly successful career as a director.
- Absence Makes the Heart Go Yonder: Dunn has a girlfriend back in New York. After being with Tonia Maria, he takes out a picture of him and his girlfriend, takes one wistful look, puts the picture away, and arranges to meet Tonia Maria again.
- Adaptational Heroism: In the O. Henry short story the Cisco Kid is pretty much The Sociopath, killing for sport, responsible for 18 murders. Here he is a sympathetic anti-hero. This movie pretty much Covered Up the O. Henry character, as the more sympathetic version of the Cisco Kid became the basis of all the many adaptations that followed.
- Anti-Hero: The Cisco Kid is a charming and affable bandit who sticks to robbing bank stagecoaches and the like, and seems to avoid killing people if he can help it. But he will kill you if you come after him, and he arranges a terrible revenge when he finds out that Tonia Maria has betrayed him.
- Best Served Cold: The Kid thinks about just getting his gun out and shooting his girlfriend and her new lover. But instead he decides to devise a plan that will hurt both of them as much as possible.
- Bond One-Liner: Trope Maker, probably, and the last line of the film after the Cisco Kid has tricked Mickey into accidentally shooting Tonia Maria to death.Cisco Kid: Her flirtin' days are over...and she's ready to settle down.
- Brownface: Warner Baxter and Dorothy Burgess, two very white people playing Hispanics.
- ...But He Sounds Handsome: The barber is commiserating with his customer, whom he does not know is the Cisco Kid, about what a rascal the Cisco Kid is. When the barber wonders about the Kid's supposed success with the ladies, the Kid says "But he may be very handsome."
- Buxom Is Better: Dunn brags about his girlfriend back in New York, saying "She has more curves than a scenic railway."
- The Dandy: The Cisco Kid wears an ornate outfit with fancy trimmings. He is shown getting a shave rather than look scraggly like the typical bandit. He has the barber prepare him a fancy bath. And he tells Mickey that he uses perfumes so he'll smell nice, which leads Mickey to call him "Fauntleroy."
- Feed the Mole: After the Cisco Kid finds out that Tonia Maria has betrayed him, he tells her that he's leaving town, which prompts her to write a note to Dunn telling him to come and get the Kid. The Cisco Kid then takes a terrible revenge by intercepting and altering that note.
- Getting Crap Past the Radar: The Kid tells Dunn that the ladies call him "conejito"..."little rabbit." Dunn pauses for a second, then grins lecherously and says "Are you that fast?"
- Known Only by Their Nickname: The Cisco Kid doesn't seem to have a real name. Even his girlfriend calls him that.
- Laser-Guided Karma: Tonia Maria gets shot dead by her new lover and Mickey has to live with the fact he killed her.
- Miles Gloriosus: Charlie the stagecoach driver has a gun, but meekly hands it over before handing over the Wells Fargo cash box to the Cisco Kid. Later, he insists that if only his gun hadn't gotten stuck in the holster, he totally would have shot the Kid dead.
- Off-into-the-Distance Ending: The Cisco Kid, after arranging for the death of Tonia Maria at the hands of Dunn.
- Pet the Dog: The Kid never robs from individuals, only from institutions like banks. When he finds out his barber lost $87 that took him 6 months to save up, he gives him the money back. He also takes a pretty broach off a woman in a stagecoach and then pays her its worth.
- Playing Possum: The Kid acts as if he was fatally wounded by a trio of cattle rustlers. He waits for them to get close and then guns two of them down.
- Really Gets Around: If Tonia Maria isn't actually a prostitute she's definitely the town bicycle (but she's probably a prostitute). She has to push a gentleman caller out the back after the Cisco Kid shows up. Literally within a couple of minutes after the Kid leaves, she's cozying up to Dunn when he arrives at her little house.
- Tranquil Fury: The Kid remains composed as he goes about planning to kill Tonia Maria, even flirting with her as usual so she doesn't suspect thing. Meanwhile he's enraged inside all the while.
- The Trope Kid: The Cisco Kid.
- Verbal Irony: The barber and a couple of customers in the barber's shop talk big about how they'd take down the Cisco Kid if they ever got the chance. Meanwhile, the Kid is laying back in the barber's chair, getting a shave.
- Villains Out Shopping: The Kid and Dunn take time to go get shaved while their in town in-between robbing stagecoaches and hunting the former respectively.
- "Wanted!" Poster: The Cisco Kid is introduced holding his own poster, which reveals that he is a bandit and there is a $5000 reward for killing or capturing him.
- Women Are Wiser: Zig-zagged. Tonia Maria is shown to be quite foolish. But the old woman Tonia Maria lives with chastens her several times to change her ways before the kid finds out, seeming to know what will happen. She doesn't and pays the price. She also figures Tonia Maria has it coming and sends the forged note by the Kid without objecting.
- Your Cheating Heart: Tonia Maria cheats on the Cisco Kid whenever he's away. Dunn likewise has a girlfriend but just shrugs and keeps right on getting into a relationship with Tonia Maria.