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I would give him or her four or five records to listen to and ask him/her to listen to them a few times to figure out what they like. My list would be: Dave Brubeck: Time Out; Miles Davis: In a Silent Way; Bill Evans Trio: Waltz for Debby; Herbie Hancock: Head Hunters; The Pat Metheny Group. If it's only one, then Dave Brubeck's Time Out.