50. Mark Winkler & Cheryl Bentyne: “Cool”
From Winkler’s Till I Get It Right (FreeHam, 2008)
Co-written by Winkler and Marilyn Harris, inspired in part by a JazzTimes review of his previous album, Sings Bobby Troup, “Cool” builds upon various urbane references—swimming pools, Chet Baker, martinis, beat poets, Jaguar XKEs—to shape a chill ode to hipsterism. The icing on this delectably soigné exercise in Troup-worthy wordplay is the addition of Manhattan Transfer’s Cheryl Bentyne. Where Winkler plays it relatively straight, cast as the unhip party guest trying to fit in, Bentyne oozes sexy sophistication while elevating Winkler’s self-deprecating schlepper to one of the cool kids.