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If you've ever seen the infamous video of David Bowie's Christmastime duet with Bing Crosby, then you know musicians are capable of the most imaginative (and baffling) collaborations. Sometimes they do it for the money. Sometimes it's to reach an audience they otherwise might not reach. And sometimes it's out of sheer love for musical adventure. On this edition of All Songs Considered we look at odd pairings, some brilliant, and some just so very, very wrong. Host Bob Boilen talks with producer Robin Hilton, NPR Music editor Stephen Thompson and All Songs summer intern Lindsay Sanchez about some of the odd pairings they've loved and loathed over the years.