If someone bet me and gave me 100 tries to make Bob's shot once, I wouldn't even attempt. I'd just pay off.
Even with the chalk cheat Bob uses on the last shot. ...
I think with a little instruction and practice, you could make the gaff shot one in 20. Seriously.
Retold: In a league I ran for while, there was a player who was roughly APA-4 level. He had seen my one pocket 93-degree cut shot. He asked me to show him how to play it. I said, "Sure," since I wasn't doing anything else. All I had to say was "More left," and "Aim fuller." Within less than 10 shots, he hit one shot that was a 110-degree cut. Yes, the object ball was chalked.
The guy had the tremendous advantage of being willing to try hitting the ball that far off-center. Many players at that level have learned -- or their arm has learned -- that they must never hit the ball more than a little from center, and they will come towards the center on every spin shot.