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Jim "Boy" Calloway is an antagonist in Red Dead Redemption 2, appearing in the mission "The Noblest of Men, and a Woman". He is a former gunslinger encountered by the player (either Arthur Morgan or John Marston depending on at what point the player accepts the mission) who the player is tasked with finding information on.
He is voiced by Frank Ridley.
Calloway is a former gunslinger and outlaw. In his prime, Calloway was the fastest left-handed draw in the Wild West. He was rumoured to have once killed fourteen men in a fight at Lewsey Hollow and was accused of murdering the Newton Twins, two outlaws he used to ride with, in 1876 (although he denies this). However, according to his former associates Calloway was not as brave and heroic as his reputation suggests and would usually run away from a fight. He vowed revenge against state marshal Slim Grant in 1882 after Grant killed his cousin Ged in a duel; however, when challenged to a duel himself Calloway fled town rather than face Grant.
During the optional mission "The Noblest of Men, and a Woman", the player comes across Calloway drunkenly passed out in Keane's Saloon, Valentine, being interviewed by his biographer Theodore Levin. Levin asks the player to track down outlaws Black Belle, Billy Midnight, Emmet Granger and Flaco Hernández, who used to know Calloway, and get quotes for his biography. The player tracks down each of them in turn to interview them, but Black Belle is the only one to co-operate, telling the player that Calloway was a drunken, incompetent coward, not a hero. Billy, Emmet and Flaco all attempt to kill the player and are killed in self-defence. The player returns to Valentine upon finding all four outlaws but fails to find Calloway and Levin, who have relocated to a riverboat in Saint Denis.
After the mission "A Fine Night of Debauchery", the player tracks down the riverboat on which Calloway and Levin are staying. Levin is informed of the situation with the outlaws and decides to credit Calloway with killing Billy, Emmet and Flaco. However, Calloway does not want this made-up glory. Instead, Calloway asks the player to capture and bring back Slim Grant so he can have the duel he should have had in 1882. The player obliges and brings Grant to a meeting point at Brandywine Drop, New Hanover. Calloway confronts Grant and demands he fight him. Grant refuses, citing Calloway's refusal to fight him years ago, and attempts to walk away before an enraged Calloway shoots him in the back, killing him. Immediately realizing the dishonour in this, he challenges the player to a duel in order to reclaim his honour. The player easily wins the duel and shoots Calloway dead.
A few days later Levin completes his biography of Calloway and sends the player a copy. The book is shown to be more or less a complete fabrication, crediting Calloway with killing Billy, Emmet and Flaco and claiming that he was fatally shot in the back by Slim Grant after mortally wounding him.
Red Dead Revolver
Red Dead Redemption
Read Dead Redemption: Undead Nightmare
Red Dead Redemption II
Chapter 4: Saint Denis
Red Dead Online