Songs I Wish I Had Sung the First Time Around was Bing Crosby's fourth album for Decca and his fifth LP, recorded and originally released in 1956 on vinyl as Decca DL 8352. This was a concept album of sorts as Bing covered some of his musical rivals' big hits, such as Al Jolson's "April Showers" and Nat King Cole's "Mona Lisa". The jazz historian Will Friedwald wrote that the album "was essentially Crosby's way of acknowledging that he wasn't the only male singer to create hits and standards."