In Red Dead Redemption you can be play sheriff or bandit, but as Rockstar games usually go, the game is far more... colorful, if you play bad guy.
Most people will end up tying the damsel on the trails, either for the sinister enjoyment of seeing her turn in a red mist or for achievements. After a while, I guess, the train driver, at first perhaps scarred by the ordeal doesn't even care anymore and 50 years later probably got hired by TF2 industries to drive around on Well.
If someone make a game in which you can kill a whole hooker city by blowing it with an atomic train, it would be an instant success.