Like Neil Diamond, Barry Manilow embarked on a transition during the 1990s from being a contemporary pop singer/songwriter to being an interpretive singer on the model of Tony Bennett, who achieved a career resurgence around the same time with a series of thematic albums.

Manilow followed 1991's Showstoppers, an album of songs from Broadway shows, with Singin' with the Big Bands, which found him covering swing-era standards, in some cases accompanied by the ghost bands of Tommy and Jimmy Dorsey, Duke Ellington, Harry James, and Glenn Miller.

Les Brown & His Band of Renown were still active, and he backed Manilow on a rendition of his hit "Sentimental Journey." For the most part, the songs covered were known more for their instrumental power than for the vocals of people like Bob Eberly and Ray Eberle, and Manilow matched them, while soloists re-created the signature sounds of the big band musicians and the arrangements were subtly updated.

So, for example, when Manilow sang Benny Goodman's "And the Angels Sing," he equaled Martha Tilton's vocal, and Warren Leuning aped Ziggy Elman's famous trumpet solo.

Manilow got in more trouble with songs like "Sentimental Journey," originally sung by Doris Day with a marked sultriness he didn't even try to evoke, and with Frank Sinatra trademarks like "All or Nothing at All" and "I'll Never Smile Again." Born just after World War II, Manilow seemed to respond to the effervescence of the sweet swing sound, but to have no grasp whatsoever of the underlying longing and pain that went with and informed these songs of wartime separation.