“You can be my wingman anytime Maverick.”
“I’ll be your huckleberry.” ‘Doc’ to Ringo
Creepy is the word for Curley, that’s for sure.
I don’t remember actors like John Wayne, Clark Gable, Lee Marvin or Kirk Douglas talking like that.
They expressed their feelings by beating the hell out of one another.
IIRC that is Old West slang for I'll Oblige you... So in the Context of Doc to Ringo "I'll draw on you and I'll send ya ta hell and carry you to your grave."