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Before the main storyline, Chris showed up in Widow's Patch and took control of the town from Sheriff O'Grady. His size and boisterousness attracted many lowlifes to him, and he was soon in command of a small army of misfits and small-time crooks. He abstained from killing the Sheriff, presumably due to the charms of his daughter, Katie O'Grady.
Ugly Chris is encountered during the mission "Ugly Streetfight". When Red Harlow arrives in town looking to collect the bounty on Bloody Tom, one of Chris' men, Udo Kang shoots Red's dog, killing it. The resulting gun battle leaves Chris and his entire gang dead.
- “Whoo, easy on those baked beans, sheriff!”
- — Chris Bailey after farting
Red Dead Redemption multiplayerEdit
"You could start your own side show with that face!"
"Come on! Smile! You'll be dead soon."
"Don't run away, little chicken!"
"Hope your thoughts are clean, 'cause I'm gonna put a window in your skull that'll show everything."
"You're about to see crazy like you've never seen it before."
"You're such a joke, you've cheered me up."
"You wouldn't know your ass from a hole in the ground."
"I've seen leopards shoot straighter than you!"
"Didn't yo mama tell you not to play with guns?"
"Come on then, chicken liver, take your best shot!"
"It reeks of cowards around here."
"Does yo mama know you're out this late?"
"Whatta ya think this is? The goddamn 1880's?"
"Where do you want your new asshole?"
"Christ alive, and I thought I was ugly!"
"Come on! Don't point at the tub if ya can't back it up."
"I've seen tougher looking newborn babies than you."
"Just give it up now! Ain't nobody gets by me!"
"You look about ready to soil your britches."
"You're gonna spend the rest o' yo days on your back. Just like yo mama."
"So you're tough now, are ya?"
"I told you not to make me mad!"
"What's wrong? You look jumpier than a far on a griddle."
"You gettin' tired old timer? Let me help you."
"You look dumber than a shit house rat."
"I'm ugly, but you look like the east end of a horse goin' west."
"You ain't even worth the scrapings of a hound dog's ass!"
"You must have a real bad death wish."
"You couldn't even kick the shit outta your own pants!"
"I don't remember orderin' the yella' liver."
- Ugly Chris has a red bandage wraped around his right wrist and part of his right hand, very similar to Red Harlow's bandage used to cover up his scorpion scar.
- In Red Dead Revolver, it seems as though Ugly Chris is black, but in Red Dead Redemption, he is changed to white.
- He is listed in Sheriff Bartlett's Journal under the Ugly Chris' Gang section.