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".

Crosby recorded the songs in April 1956 in Los Angeles, with orchestrations by arranger Jack Pleis.

[2] Bing Crosby Enterprises and Universal Music issued a deluxe, 22-track version of Songs I Wish I Had Sung in 2014 which added many radio tracks to the original LP.

"[4] All personnel as listed on the Bing Crosby Enterprises and Universal Music deluxe, 22-track CD version: Buddy Cole (piano); Vince Terri (guitar); Don Whitaker (bass); Nick Fatool (drums); Skeets Herfurt, Harry Klee, Ted Nash (alto saxophones); Jules Jacob (tenor saxophone); Robert Lawson (baritone saxophone); Lou Raderman, Henry Hill, Ben Gill, Victor Arno, Toscha Seidel, Sam Cytron, Saul Steinberg, Nick Pisani, Jack Pepper (violins); Abe Hochstein, Milt Thomas, Raymond Menhennick (violas); Armand Koproff, Ossip Giskin (cellos).