Canciones populares de esta etapa son "I'll Never Smile Again" (el mayor éxito), "Fools Rush In", "Stardust", "Everything Happens To Me", "This Love of Mine", "I'll Be Seeing You", "This Is The Beginning of The End", "East of The Sun", "Without a Song", "Blue Skies", "Violets For Your Furs", "The Night We Called It A Day", "The Song Is You" y "Night And Day" (clásico este último de Cole Porter que Sinatra grabaría en multitud de ocasiones).