Director Joseph Crehan as Old Gentleman Ethel Griffies as Voice Teacher Frank Faylen as First Reporter Billy Gilbert as Steel Worker Grace Hayle as Rural Mother Johnnie Morris as Newsboy Selmer Jackson as Doctor Sig Arno as Ballet Master Ralph Faulkner as Fencing Master Earl Dwire as Mac, the Accountant Harry C. Bradley as Conductor Wally Maher as Reporter George Eldredge as Reporter Stanley Price as Reporter George Guhl as Piano Mover Jimmie Dundee as Second Piano Mover Max Wagner as Third Piano Mover Ralph Sanford as Uniformed Doorman A.S. 'Pop' Byron as Stage Doorman Allen Fox as Photographer Fritzi Brunette as Cutie's Mother Edwin Stanley as Gerry Member Ottola Nesmith as Elderly Lady Jack Pennick as Prizefighter George C. Pearce as Gerry Society Member Doro Merande as Gerry Society Woman Frances Raymond as Gerry Society Woman Kenneth Wilson as Ken Billy Simms as Spike Donald Brenon as Judge Patti McCarty as Patsy John Andrews as Andy Danny Daniels as Blackie Don Hulbert as Duck Gloria Atherton as Curly Darryl Hickman as Boots Dorothy Babb as Dottie Dante DiPaolo as Turkey Tommy Batten as Bats Mary Ellen Bergren as Ivories Gene Collins as Dummy Eugene Eberle as Whitey Dolores Dianne as Rusty Joe Geil as Red Richard Humphries as Chicago Jackie McGee as Lucky Joyce Arleen as Toots Roland Dupree as Frenchy Marilyn Marlin as Ginger Patsy Parsons as Cookie Jean Ruth as Butch Leon Tyler as Big Ears Howard Smiley as Skipper Marilyn McKay as Cutie Dena Penn as Penny Soundtrack "Jimmy Valentine" (Edward Madden / Gus Edwards) sung by Bing Crosby. "A Man and His Dream" (James V. Monaco. Johnny Burke) sung by Bing Crosby. "If I Was a Millionaire" (Will D. Cobb / Gus Edwards) sung by Bing Crosby and children. "Go Fly a Kite" (James V. Monaco / Johnny Burke) sung by Bing Crosby and children. "I Wonder Who's Kissing Her Now" sung by Bing Crosby. "Sunbonnet Sue" (Will D. Cobb / Gus Edwards) sung by children "In My Merry Oldsmobile" sung by Bing Crosby and children. "Darktown Strutters' Ball" sung by Linda Ware "An Apple for the Teacher" sung by Linda Ware, Bing Crosby and children. "School Days" sung by Linda Ware, Bing Crosby and children. "Waltz of the Flowers" sung by Linda Ware "Still the Bluebird Sings" (James V. Monaco / Johnny Burke) sung by Bing Crosby and children. Bing Crosby recorded a number