|“||I slayed my dragons years ago.||„|
|—Jim "Boy" Calloway|
In his prime, Jim "Boy" Calloway was considered the fastest left-handed draw in the Wild West and is rumored to have “killed fourteen men in a fight at Lewsey Hollow”, as detailed by his biographer Theodore Levin. Levin also mentions an incident at Sylvia's Saloon in 1876 involving the Newton twins, who Calloway was alleged to have killed (although Calloway himself dismisses this as "just a lot of bunk" and says that one of the twins was actually a woman). In the same conversation, Levin asserts that Calloway and the Newton twins were friends at some point and that they "rode the Alabaster trail together" in 1873.
By 1899, Calloway is considerably older and has trouble remembering the exploits of his earlier days, much to the dismay of Levin. In his younger days, he crossed paths with Emmet Granger, Flaco Hernández, Billy Midnight, and Black Belle. In addition to meeting these other well-known gunslingers, Calloway developed a feud with future New Hanover State Marshal Slim Grant, due to Grant killing his cousin.
Despite these many tales, Black Belle says that the legends surrounding him are mostly fiction and that Calloway usually ran from a fight. Additionally, Slim Grant says that he and Calloway were going to duel over the death of the latter's cousin shortly after it happened, but Calloway never showed up.
Events of Red Dead Redemption 2
Calloway is drunkenly passed out at Keane's Saloon in Valentine, where the player can approach Theodore Levin to ask about who Calloway is. Levin asks the player to get quotes about Calloway from fellow gunslingers he knew, in order to help him write Calloway's biography. While the player is tracking down the gunslingers, the pair then relocate to a riverboat in Saint Denis. After the player catches up with Levin in Saint Denis with pictures of Emmet Granger, Flaco Hernández, Billy Midnight, and Black Belle (with all except Black Belle having been killed in duels with the player), Levin wants to give Calloway the credit for defeating them. Calloway, however, doesn't want to be given the credit and instead asks the capture of his old rival, Slim Grant, with the likely intention of proving himself by defeating him in a duel.
Once Grant is brought to Calloway, the two have an argument which results in Calloway challenging him to a duel. Slim Grant refuses and walks away, only to be shot in the back by Calloway. Upon realizing that he had shot his opponent in the back - which was considered to be dishonorable and cowardly - Calloway is reassured by the player but, feeling insulted, he challenges the player to a duel in a final attempt to regain his pride, which he is slain in.
Levin subsequently covers up the player's involvement by saying that Calloway was shot in the back by Slim Grant after mortally wounding the latter in a duel. He rewrites Calloway's history even further by saying that he was the one who defeated Emmet Granger, Flaco Hernández and Billy Midnight in duels.
Calloway has the fastest drawing speed of all NPC duelists in Red Dead Redemption 2, and trying to beat him fairly, by waiting for the draw meter to fully charge, will likely result in the player losing. Even if the player charges the meter as fast as possible and immediately shoots as soon as it has fully charged, it will only cause a draw.
Because of this, the recommended way to beat Calloway is through cheating, which the player won't lose Honor from due to the duel being part of "The Noblest of Men, and a Woman" side mission. Players should only partially charge the draw meter, to make sure they do not miss, before shooting. Otherwise, they should immediately activate Dead Eye, manually adjust the aim and then shoot. Regardless of where he is hit, Calloway will die from a single shot.
- Red Dead Redemption 2
|“||Jim was a hero. Women loved him and he shot men in the face, not the back. Death did not frighten him, only dishonor did.||„|
|—Calloway's description in Wild West Heroes, no. 132|
- Calloway and Ansel Atherton are the only explicitly left-handed characters in the Red Dead series.
- Calloway's Revolver is an obtainable weapon. When inspected, the engravings on it read: "Canis Canem Edit" - a Latin phrase meaning "dog eat dog", which is a synonym for "every man for himself" or "survival of the fittest". This is potentially a reference to the European/PAL title of another Rockstar game, known in North America as Bully.
- Levin's published fabrication of Calloway's death omits the player's involvement entirely; even the in-game Compendium incorrectly states that Calloway was shot in the back by Slim Grant, in his unique revolver description. Looking at the protagonist's journal reveals they do not mind however, preferring to 'slip back into obscurity.'
- In the book "Wild West Heroes, No. 132", Calloway has an encounter with Landon Ricketts while trying to infiltrate a Mexican besiegement of a US Army fort. Ricketts initially holds Calloway at gunpoint and they briefly converse, with Ricketts letting Calloway know the reality of the situation (bandits control the fort, and the leader of the Mexicans is after the same man as Calloway) and join forces. It is not known to what extent this story is true.
- The story mentions Calloway as a lawman with a history of being a rancher and an Army scout, and in the story, he was after Clanton Fitch, who killed his brother in Blackwater. None of this is stated or alluded to by Calloway, Levin, or any other source of information on him, although it's not necessarily an impossibility given Calloway's alleged experience as a gunslinger.
- The Valentine Butcher will reveal that Jim “Boy” Calloway and Ben Calloway are cousins while shopping at his store.