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Beat Hollister.

If you take a barrel of TNT from the Badlands mine and put it on the north end of the old abandoned house's chimney. The explosion will open up a hole in the ground with unlimited ammunition. To get there, get out of Dodge City. Make your way to the Badlands (use your map for directions) and head into the field that has several horses and buffalo. The house and the mine with the TNT will be right next to you.

Finish the Hunting Missions.

Beat Reed.

Sneak up on Hollister and shoot him once. Then, run off and get behind a rock on top of risen ground in the middle of the arena. When he is circling the rock you are behind, start circling as well. He will eventually stop and yell at you to come out. He should pace back and forth slowly while you hide behind the rock. When he stops and is not facing you, shoot him in the head. Perform this until the point that he becomes too smart to fall for it again. By then his health should be low enough so that you can run out and keep shooting while strafing. After you have gotten his health down all the way there will be a intermission sequence. Look at your compass at the bottom of the screen. He is the red dot. Find him and he will run at you. Run, but keep firing at him with your pistols and he will die.