It probably struck a number of Dixieland and swing jazz fans as odd when they first found out that they didn't have to settle for just listening to old records from yesteryear. Visitors to Disney World, for instance, could make 60 years of jazz "progress" disappear by visiting the Grand Floridian Hotel where the Palm Beach Society Orchestra held court. And while the band certainly reached back to the distant past for its repertoire, the band was much more than a nostalgia act. When You're Smiling offers a generous portion of the band's music, recorded in Lone Pine Studios in Florida in 1998. The Palm Beach Society Orchestra splits this 15-piece set pretty evenly between vocals and instrumentals, and draws the majority of these songs/instrumentals from reliable standards. Michelle Amato is featured on four songs, including "Ain't Misbehavin'" and "Don't Get Around Much Anymore," while guitarist Bob Leary sings "It's a Sin to Tell a Lie" and "A Kiss to Build a Dream On." This is happy music, with trombones, clarinets, and cornets creating a lively Dixieland mix. Part of the strength of this band lies in its versatility, a quality that manages to keep even the most familiar piece fresh. Fans of older styles of jazz will enjoy When You're Smiling, but so will anyone who likes the kind of music that makes the listener feel good.
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AllMusic Review by Ronnie D. Lankford, Jr.