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Miles Davis -"Kind of Blue" and Dave Brubeck "Time Out" are great starts. They are easy to listen to, catchy, but so musically deep that you can listen to them over and over again and find something new.
Monk - "Straight, no chaser". As you listen to other jazz artists, you'll hear them do versions of the songs on that album. So why mess with the covers, go straight to the source.
There are bunch of songs you could listen to just to get a feel for the Jazz genre. "One O'Clock Jump" by Count Basie, "Take the A Train" by Duke Ellingtons Orchestra, "A Night in Tunisia" by Gillespie. "Caravan" - listen to several artists do this song. It's interesting to hear different takes on it.
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