Python had a great community though, and the Python Software Foundation went out of it's way to make people feel accepted in the community. And frankly programming is often more of a social activity than most people realize -- particularly for new programmers.
So new programmers tended to lean towards python, because the resources to lean on others were there. And people like Raymond Hettinger, Naomi Ceder, Ned Batchelder, and Yarko Tymurciak were approachable even if the BDFL wasn't.
Looking at the hip n cool languages, not just Python for scripting but surely Go and to some extent Rust as well for native stuff (Dart for scripting also but it didn't outright "win"), these are mostly languages that deliberately simplified things. Yes, even Rust - it needs to be compared to C++ and its biggest feature is basically that it doesn't let you do all the things C++ does, within a very similar model.
The only language that I heard is going against these trends (but I'm largely clueless what it's actually like) is Julia which sort of has its own "lay" niche like Perl did back in the day, and is mostly winning based on the premise that it's a performant scientific language.
The industry obsesses over costs of adoption, stability, maintenance; in short: how to get the most out of the least actual new development. It does make quite a lot of sense, to be honest, although sometimes it's really demotivating at an individual level.
And frankly, "learn the language, duh" usually comes up when the language is complex or unintuitive for no practical purpose. Of course there will be people who always complain if they have to learn anything but I don't think they make the majority, or even a significant minority, in the software engineering world. "Learning the language" is only as much of a virtue as the language itself serves its purpose, which includes easy of use and the readability of someone else's code.