What people forget is that JIRA is a more complex product. Probably by orders of magnitude. There is SO MUCH you can do with JIRA and so many different integrations that while it's very clunky, I feel they don't get enough credit for managing all that complexity in some manner that is at last
somewhat sane. In fact, clunkiness comes with that territory of complexity, there's just really no way around it (well, this is a simplifying statement, but the point is that different tradeoffs would have had to be made).
That's why a lot of JIRA to Asana comparisons don't really hold up. The problem arises when a small team that needs a quick and simple to-do list start using JIRA and then compare it to other solutions which do probably 1/100th of what JIRA does. If you don't need the cruft that JIRA comes with, then that's fine...but there are genuinely orgs that do need it.
Now I'm no fan of JIRA. I don't really love it, and I fall under the camp that tolerates it. However, even then I can appreciate it for what it is and what it means to do. They can do better of course...but we can't simply compare directly between something like JIRA and Asana.