I think the popularity of Python is due to its rigidness. Since it's easier to write inscrutable Perl programs than Python, and Perl is much more TIMTOWTDI, I can see many new programmers struggling to parse Perl, even well written Perl, while they have little trouble parsing Python, even bad Python. Perl's misplaced reputation for write-only doesn't help. But somehow Python's meaningful whitespace doesn't cause the same problem? (I thought "we" learned our lesson with whitespace in make? Oh wait, was Python entrenched before that lesson was fully realized.)

That isn't to say that they can understand one better than the other, because it's the larger constructs that the story hangs on. It's hard to beat a good abstraction hierarchy, and judging by may samples in the wild, it's hard to create one too.

I recall from my university days, comparing Fortran, Pascal, and C. Pascal was a "teaching" language, so had all the rails up. As such, it was fairly easy for a CS newbie to get somewhere, with a book and a compiler alone. Pascal was popular in industry where engineers with little CS training had to write complicated software. Pascal still had the full rails up. One of our systems actually had a Pascal interpreter written in C, because the C compiler was free, but the "customer" wanted Pascal for the non-literate engineers. (Of course, it had none of the features unique to Pascal, such as sets, and did not have pointers. Even though it was for testing silicon chips, and sets of pin names and numbers would have been useful.)