“When You’re Smiling” was written by Mark Fisher, Larry Shay and Joe Goodwin. According to Thomas S. Hischak in The Tin Pan Alley Song Encyclopedia, “Seger Ellis popularized the tune, but it was Louis Armstrong who made it a standard.” (Ellis was a songwriter/pianist/vocalist popular in the ‘20s and early ‘30s.) Armstrong first recorded it in 1929 and then again in 1932 and 1956. His is the version heard in the 1984 film The Cotton Club. The song has appeared in several other films, including Meet Danny Wilson (1952) in which it was sung by Frank Sinatra, and it was the title cut of a 1950 movie in which it was sung by Frankie Laine.

The lyric advocates a cheerful attitude because “when you’re smilin’, the whole world smiles with you.” Conversely, “when you’re cryin’, you bring on the rain.”

“When You’re Smiling” has been recorded by vocalist Eddie Jefferson; the big bands of Count Basie, Stan Kenton, and Duke Ellington; the Dave Brubeck Quartet; saxophonist Art Pepper; guitarist Joe Pass; and many Dixieland groups. In The Swing Era: The Development of Jazz, 1930-1945, Gunther Schuller highlights Billie Holiday’s recording of the song: “‘Lady Day,’ so named by Lester [Young], and ‘Prez,’ so named by Billie, were obviously musical soulmates and inspired each other.... ‘When You’re Smiling’ (January 1938) is a superior example of their collaboration....”

Recent recordings, however, are sparse. Drummer Bill Stewart and his group of contemporary musicians (Joe Lovano, Dave Holland, and Marc Copland) improvised on it in 1990; trumpeter Warren Vache featured it with the New York City All-Star Big Band in 2000, and Mike Barone’s Big Band recorded it in 2005.