Ruby vs. Python is a frequent topic on HN [1] [2] [3] [4]. These discussions invariably focus on web development because of (a) the nature of HN, and (b) the fact that most Ruby applications are web applications.
I located all those references by my comment history, so I participated in all of the discussions. Generally I pointed out how painful Ruby's syntax is, how beginner-unfriendly the syntax plus the complexity of Rails is, how favorably Python contrasts, and then posed this Ask HN's very question.
The discussion thereafter often rapidly degenerated into a flame war, but one time I got some rather informative answers [5].