Just curious. How many of you can sight transpose a chart on the fly, especially an up-tempo number? Just speaking for myself, but I find it much easier to transpose a tune I already know well, in fact, I really CAN'T transpose even a chord (fakebook) sheet on the fly if it complicated and I really don't know it. I don't think so much 'transpose' as much as just playing it in a different key (same thing but not really - it's a mental thing). Of course, IF I have to play it not in the original key (I have always learned all tunes in the original key), then the new key had better be C, Eb, F, G, Bb, or their relative minors

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Most guys that play mostly jazz know most of the 100-150 most popular so-called jazz standards. In most jazz clubs, it's going to be either that or original material. Doesn't get old though, as most jazz audiences actually WANT to hear something familiar, just with a new take on it. At least that's been my experience. They are much more tolerant of an oft-played tune than a lousy performance. As for the (jazz) players, it always a pleasant challenge to see what else you can do with it (the tune). You rarely see a chart in a jazz club if the group is less than five players. Not saying it's good or bad, just the way it is.
chas
I used to be able to transpose on the fly, even a new chart, as long as it was not "dot heavy". Tempo is not really an issue as it was "ground" into me when I was taking lessons to ALWAYS read a bar or two in front, which of course is now an ingrained habit! So I can be playing one but reading the bar two even sometimes three in front getting my mind onto a coming change.
Sadly these days, I have let those skills wane as more and more I simply get lazy and just use the transpose button, especially to the 4+ sharp keys (always had a problem with sharp keys, but not so much with flats, go figure hey!)
Transposing is a skill that needs constant practice to maintain adequate ability in my view...It's not like just "knowing chords" it is more than that, and the people who cna do it well, impress the hell out of me!!
Interesting point re the jazz tunes Chas...That is my experience too, as the number of jazz tunes I have on the iPad is only about 120 or so...and the folks I play to don't seem to tire of those anywhere near as much as the "popular" songs. Could also be that I rarely play the same jazz tune twice the same way, if ever!! Which sorta kinda reinforces what you are saying

Dennis