The Village Vanguard is the most famous club in jazz history. More than 150 albums have been recorded there, including historic music by Sonny Rollins, Bill Evans, and John Coltrane. Ashley Kahn wrote that recording at the Vanguard is "a rite of passage for modern jazz players." That's accurate.
I've only been to the Vanguard once. Kerrie and I went on a Monday night to see the Vanguard Jazz Orchestra, and it cost the two of us $60 to walk through the door. Manhattan rent aside, that's ridiculous. I have no objection to an honest business trying to make a profit; but there's a fine line between cultural landmark and tourist trap. In this case, that line is economic.
If you'll pardon hyperbole, a jazz fan's visit to the Vanguard is like a Muslim's pilgrimage to Mecca: It's got to be done. And although you're essentially paying for prestige, I can't deny the Vanguard books serious artists. If you're looking to hear music and can't be bothered to browse listings, the Vanguard is a sure bet. But the fact that jazz is subsidized by affluent white folks is an unfortunate reality that we shouldn't propagate; and like the price of Red Sox tickets, it's a shame to think that a couple of college kids can't catch a show without chipping a week's pay.