I'll Never Smile Again

This song was written by a Toronto-based songwriter named Ruth Lowe, who composed it out of the despair she felt when her husband, Harold Cohen, died in 1939 after an operation went wrong (in glorified tales of this story, Cohen was a Canadian fighter pilot who was killed in action). Lowe's sentiment was that she could never love another, or even laugh again, since her true love was killed. To give the song a more universal appeal, she made it about a breakup, including the lines: Tears would fill my eyes My heart would realize That our romance is through

The first performance of this song was by Percy Faith's orchestra on CBC Radio in 1939. Tommy Dorsey, whose orchestra was one of the most popular in America, received a copy of the song and recorded it with his young vocalist, Frank Sinatra. Issued as a Tommy Dorsey single, it was the first-ever #1 on Billboard's singles chart, the magazine's precursor to the Hot 100.

This became one of Sinatra's most popular songs, especially later in his career when it was included in most of his sets. His daughter Nancy explained in the documentary Sinatra: All or Nothing at All, "That song, it followed by dad his whole life, and I think it was probably because so many people identified with it in the first place, with their personal losses."