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You asked for one, so I'll respect that, but it's hard. I've done two radio shows, one where I played 4 hrs of just Sun Ra, and another where I played 6 hrs of same. But for one "Classic" Jazz Record, I'm going to go with Miles.
Lots of other people are covering Kind of Blue, so I'll take the other extreme: On the Corner. It was hated by jazz purists when it came out, because he fully embraced electronic instruments and funk beats. Decades later it was listed by many a punk/funk artist as a major inspiration, but it goes beyond that, and way beyond the "fusion" ghetto as well. It's actually quite melodic at times, though always rhythmic, and it takes the classic spirit of jazz and transports it to a whole new playground.
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