Every time I gamble in game I always draw a gun.

Having to win a few hands after hitting like 8 times in blackjack was definitely the most frustrating for me. Usually when I start to do all the challenges I try and finish the gambling ones first so I can just get it over with.

Horseman 9. You have to ride from Van Horn to Blackwater in under 20 minutes, without touching water. I had the most stupid luck while doing it. I got ambushed multiple times while doing it, and ran over by a train.