Few pop singers of the 20th century had a greater impact on how vocalists approached their craft than Bing Crosby. Bing was one of the first singers to understand how to use the microphone to his advantage, and his phrasing brought jazz and blues influences into the mainstream in a new way, while maintaining an infectious, upbeat, easygoing vocal personality. In 1956, Crosby recorded the album Songs I Wish I Had Sung the First Time Around..., in which he paid homage to some of his favorite singers by interpreting their signature songs, including Al Jolson ("April Showers"), Nat King Cole ("Mona Lisa"), Louis Armstrong ("Ain't Misbehavin'"), the Mills Brothers ("Paper Doll"), Billy Eckstine ("Prisoner of Love"), and even his frequent comic foil Bob Hope ("Thanks for the Memory"). In 2014 the album was reissued in an expanded edition, featuring an additional ten songs with Crosby covering a handful of pop standards, as well as unreleased session outtakes.
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AllMusic Review by Mark Deming