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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.

Biography

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.

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           Official Red Dead logo.png Villains

Red Dead Revolver
Bad Bessie | Bloody Tom | Captain Bufias | Colonel Daren | General Diego | Governor Griffon | Grizzly | Holstein Hal | Longhorn Luke | Mr. N. Black | Pig Josh | Professor Perry | Sam | Smitty | Ugly Chris Bailey | The Ugly Gang | Black Gang | Jesse Lynch

Red Dead Redemption
Abraham Reyes | Agustin Allende | Archer Fordham | Williamson Gang | Bill Williamson | Dutch's 1911 Gang | Dutch van der Linde | Edgar Ross | Espinoza | Javier Escuella | John Marston | Mexican Army | Norman Deek | Randall Forrester | Seth Briars | Vincente De Santa | Bureau of Investigation | Banditos | Bollard Twins Gang | Walton's Gang | Reyes' Rebels |

Read Dead Redemption: Undead Nightmare
Undead

Red Dead Redemption II
Van der Linde gang
Dutch van der Linde| Arthur Morgan | John Marston | Cleet and Joe | Leopold Strauss | Micah Bell | Hosea Matthews | Josiah Trelawny | Bill Williamson | Javier Escuella | Charles Smith | Lenny Summers | Karen Jones | Sean MacGuire | Sadie Adler | Susan Grimshaw

Chapter 1: Colter
Colm O'Driscoll | O'Driscoll Boys

Chapter 2: Horseshoe Overlook
Leviticus Cornwall | Andrew Milton | O'Driscoll Boys

Chapter 3: Clemens Point
Catherine Braithwaite | O'Driscoll Boys | Braithwaite Family | Lemoyne Raiders | Tavish Gray | Gray Family | Leigh Gray

Chapter 4: Saint Denis
Angelo Bronte | Angelo Bronte's Mob

Chapter 5: Guarma
Alberto Fusar | Cuban Military | Levi Simon

Chapter 6: Beaver Hollow
Colonel Henry Favours | United States Army | Leviticus Cornwall | Andrew Milton | Murfree Brood | O'Driscoll Boys | Pinkertons

Epilogue Part 1: Pronghorn Ranch
Laramie Gang Leader | Laramie Gang | Mr. Abel

Epilogue Part 2: Beecher's Hope
Micah Bell | Skinner Brothers | Micah's gang | Cleet and Joe

Others
Bray and Tammy Aberdeen | Edmund Lowry Jr. | Elias Green | General Quincy T Harris | Ku Klux Klan | Curtis Malloy | Lindsey Wofford | Night Folk | Otis Skinner | Saint Denis Vampire | Jim "Boy" Calloway | Flaco Hernández | Emmet Granger | Billy Midnight | Black Belle | Ramon Cortez | Esteban Cortez | Benedict Allbright | Ellie Anne Swan | Joshua Brown | Jeremiah Compson | Camille de Millemont | Anthony Foreman | Nathan Kirk | Mark Johnson | Bart Cavanaugh | Medicine Man | Herman Zizendorf | Shane Finley | Sonny

Red Dead Online
Free Roam
Red Dead Online Protagonists | JB Cripps | James Langton | Old Man Jones
Bounty Hunter
Carmela "La Muneca" Montez | The Wolf Man | Sergio Vincenza | Philip Carlier | Owlhoot Family | Yukon Nik Borodin | Borodin's Gang | Red Ben Clempson | Red Ben Gang | Etta Doyle | Etta's Gang | Barbarella Alcazar | Seventh Generation | Virgil "The Shepherd" Edwards | Gene "Beau" Finley | Tobin Winfield | Cecil C. Tucker
A Land of Opprtunities
Amos Lancing | Teddy Brown | Teddy Brown's Boys | Jorge Montez | Alfredo Montez | Del Lobo Gang | Jeremiah Shaw | Grace Lancing
A Life of 'Shine
Reid Hixon | Danny Lee Caton

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