The Five Pennies is the life story of influential jazz cornetist Red Nichols, played here by a remarkably straight-faced Danny Kaye. The somewhat romanticized screenplay chronicles Nichols' rise from obscurity, annotates the many future bandleaders who would play with Nichols' "Five Pennies," and details his self-destructive streak and (seeming) inability to conform to changing musical tastes. Weaving in and out of the main story is a sentimental subplot concerning Nichols' physically impaired daughter Dorothy, played by Susan Gordon as a child and by Tuesday Weld (in her movie debut) as a young woman. Nichols's long-suffering wife is portrayed by Barbara Bel Geddes. The storyline occasionally lapses into sappiness and the ending is almost impossibly lachrymose, but the musical highlights save the day. Especially memorable is Danny Kaye's duet with Louis Armstrong. Among the real-life musicians who grace the supporting cast of The Five Pennies are Bob Crosby, Ray Anthony, Shelly Manne, and, as Jimmy Dorsey, Bobby Troup.
~ Hal Erickson, All Movie Guide