The concept of an album in which Bing Crosby sings "the Sinatra songbook" is a curious one on two grounds. First, "songbook" albums usually consist of songs written by a particular person, not songs associated with a particular singer, and second, since Crosby preceded Frank Sinatra by roughly a decade-and-a-half and was an idol and mentor to Sinatra, the idea of Crosby singing his pupil's songs seems to cast things in reverse. That said, this collection, assembled by Bing Crosby Enterprises for release by Collectors' Choice Music and consisting largely of previously unreleased radio transcriptions from the '50s, has much to recommend it, as Crosby puts his own stamp on some well-chosen songs tailored to his follower. As annotator Michael Feinstein points out, by the ‘50s Sinatra had eclipsed Crosby as a record seller, and songwriters were hard at work writing songs for him to sing in his movies and on his records. Interestingly, one of those songwriters was composer James Van Heusen, who had previously written songs for Crosby's movies. (In those days, Van Heusen had worked with lyricist Johnny Burke; by now he was paired with Sinatra's favorite word man, Sammy Cahn.) So, perhaps it's no surprise that, while "High Hopes" was designed for Sinatra, it also works well for Crosby, for whom it is a virtual follow-up to his hit "Swinging on a Star." Crosby also has fun with Sinatra specialty material like "Young at Heart," "The Tender Trap," and "Love and Marriage," and if he isn't interested in giving "All the Way" the drama Sinatra brings to it, he nevertheless renders the song effectively. A lot of these songs, while they might have been recorded by Sinatra at one point or another, are no more associated with him than they are with Crosby, and perhaps less so. "Imagination," for example, is a song Sinatra covered while with Tommy Dorsey's orchestra, but it was really a hit for Glenn Miller, and it was actually written by Burke and Van Heusen, which would seem to put it in Crosby's camp. A bunch of '30s standards are also featured, and they could be included in any number of singers' "songbooks." It's true, for instance, that Sinatra interpolated the 1937 song "The Lady Is a Tramp" into the 1957 film Pal Joey, but Crosby couldn't have anticipated that when he sang the version here in 1955, even if he makes a point of humorously mentioning Sinatra by name. Sinatra himself turns up for a medley with Crosby recorded in 1954, and it's too bad there isn't more of the two together on the album. The tracks vary from full orchestral arrangements featuring Crosby's longtime radio bandleader John Scott Trotter to small ensembles led by keyboardist Buddy Cole, who can be a little busy for some listeners' taste, especially when, as on "Witchcraft," he takes to the organ or, as on "Love and Marriage," the harpsichord.
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AllMusic Review by William Ruhlmann