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I enjoy some American songbook tunes that are done in different time signatures. Brad Mehldau comes to mind with songs like I Didn't Know What Time It Is and It Might as Well be Spring. I also have a few friends who I jam with but their obsession with experimenting in odd time signatures makes it difficult to continue enjoying to play with them, and I think they would be better improving their common time swing as they are not Paul Chambers or Philly Joe.

This song was recently used on Open Studio video and I am a fan of Gerald Clayton but I'm trying to understand the need to play song in in which it changes from 5/4, to 6/4, to 7/4 as a repeated form. Sure it's great for respect to have ability to seamlessly do this but what's the point?

I suppose jazz musicians often want to do something new, something that is from the present and not just copying something that was done before. There seems to me to be more point in trying something new than just playing ‘all the things’ in the same way that has been done to death a zillion times already, because this keeps jazz moving forward.
If people waited to play in different time signatures until they had the time feel of Philly Joe they wouldn’t ever get to try it. Nobody does or could have that feel today, he was a product of his time.

Just my opinion of course, and there is nothing wrong with playing in 4/4.