"On the Sunny Side of the Street" is a 1930 song, with credited music composed by Jimmy McHugh and lyrics by Dorothy Fields. Some authors say that Fats Waller was actually the composer, but he sold the rights for the money. It was introduced in the Broadway musical Lew Leslie's International Revue, starring Harry Richman and Gertrude Lawrence.
Having become a jazz standard, it was played (usually as an instrumental) by such greats as Louis Armstrong, Ted Lewis, Dave Brubeck, Earl Hines, Benny Goodman, Lionel Hampton, Erroll Garner, Dizzy Gillespie, Art Tatum, James Booker, Count Basie and Lester Young. The Louis Armstrong version was recorded in the key of C major, but it has been recorded in a range of keys; Ted Lewis recorded it in D major and Ella Fitzgerald in G major etc.
Duke Ellington's orchestra featuring Ivie Anderson recorded a live performance at the Cotton Club, April 24, 1938.
Fats Waller and His Rhythm performed the song live with Louis Armstrong and Jack Teagarden in a radio broadcast from Martin Block’s Make Believe Ballroom in October 1938. The version is included on the 1981 Smithsonian Folkways album Striding in Dixieland (FW02816).
Frankie Laine had a hit with his recording and the song also was recorded by other leading vocalists, including Billie Holiday, Dinah Washington, Ella Fitzgerald, Judy Garland, Doris Day, Keely Smith, Nat King Cole, Jo Stafford, and Frank Sinatra. Arguably the best known arrangement is found in the 1945 record by Tommy Dorsey and the Sentimentalists.