To me it seems obvious that the chained comparisons wouldn't work. I've never seen someone make that mistake before. Doing that breaks extremely easily without the fact about booleans. If a == b == c is True, then (a == b) == c is guaranteed to be False unless they are all equal to True (or 1). I often use this property of booleans to write something like sum(predicate(x) for x in lst) to count the number of items in a list satisfying a condition, or conveniently making something plural with f"thing{(len(things) > 1) * 's'}" . It's hacky but it's fun.

Since 0 is considered a "Falsy" value, then the comparison returns 'True`. No, that's the kind of thing JavaScript does. Most Falsy values (None, empty string/list/dict/etc) are not equal to False. False == 0 and True == 1 because bool is a subclass of int. You can treat booleans just like those numbers, for example True + True == 2 . This can be very useful.