In 1949, he showcased his singing abilities by recording four songs for Decca Records with the popular Andrews Sisters singing trio. Two of the songs were Irish novelties ("Clancy Lowered the Boom!" and "I Had a Hat (When I Came In)"). The other songs, Take Me Out to the Ball Game and In the Good Old Summertime capitalized on the success of two MGM blockbuster films of the same names from that same year, starring Gene Kelly, Esther Williams, Frank Sinatra ("Tale Me Out to the Ballgame" and Judy Garland and Van Johnson ("In the Good Old Summertime"), respectively. Dailey and The Andrews Sisters were an excellent match, and their vocal stylings on these selections were full of gaiety and fun.