|“||I slayed my dragons years ago.||„|
|—Jim "Boy" Calloway|
In his younger days, 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"). 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.
Now considerably older, Calloway has trouble remembering the hijinks 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 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 how he and Calloway were going to duel over the death of the latter's cousin, but Calloway never showed up.
Events of Red Dead Redemption 2
Calloway is drunkenly passed out at Keane's Saloon in Valentine, when the player is approached by Theodore Levin to get quotes about Calloway, in order to help him write Calloway's biography. 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 realising 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, Calloway challenges the player to a duel in a final attempt to regain his pride, which he is slain in.
Theodore then covers up the player's involvement by saying that Slim Grant shot Calloway in the back, after Calloway mortally wounded him in a duel. He covers up the player's involvement even further by saying that it was Calloway who had defeated Emmet Granger, Flaco Hernández and Billy Midnight in duels.
Calloway has the fastest drawing speed in all of 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 likely 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
- 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. When translated, the phrase means "Dog eat dog"; every man for himself, or survival of the fittest. This may very likely be a reference to the subtitle of another Rockstar game, Bully.
- Jim "Boy" Calloway shares the same surname with Ben Calloway, but it is unknown if they are related. There are also 3 people buried in Valentine with the surname "Calloway".
- Theodore's published fabrication of Calloway's demise has the player's involvement go publicly unnoticed; even the in-game Compendium incorrectly states how he died, in his unique revolver description. Looking at the player character's journal reveals they do not mind however, preferring to 'slip back into obscurity'.
- If Arthur Morgan helps Theodore Levin in "The Noblest of Men, and a Woman". Jack Marston right after the ending of Chapter 6 will mention the book that Arthur helps write.
- In the book "Wild West Heroes No. 132", Calloway has an encounter with Landon Ricketts while trying to infiltrate a Mexican Army Fort. Ricketts initially holds Calloway at gunpoint, and they briefly converse, before Ricketts lets Calloway continue on his way.
- It is not known to what extent this story is true, although it does mention that Calloway is a lawman, which may have been true, as it is a job that would have provided Calloway with an opportunity to become a good shooter.
- During this story Ricketts tells Calloway "Keep jumping from one side of the fence to the other, you might just get impaled on it”, which is the same line he says to John Marston in the mission "The Mexican Wagon Train".