First recorded by Roger Wolfe Kahn & His Orchestra with Harry Richman (US #13 1930).
Other popular versions by the Ted Lewis Orchestra (US #2 1930), Lionel Hampton (R&B #10 1938), Jo Stafford & the Pied Pipers (US #13 1944), Tommy Dorsey & the Sentimentalists (US #1 1945).
Also recorded by Fats Waller, Louis Armstrong & Jack Teagarden (1938).
From the wiki:”‘On the Sunny Side of the Street’ is to Jimmy McHugh, with lyrics by Dorothy Fields. But, some authors believe that Fats Waller was the composer, selling his rights for the money. (Fats Waller & His Rhythm would later perform the song live with Louis Armstrong and Jack Teagarden in a radio broadcast from Martin Block’s Make Believe Ballroom in October 1938.)
“The song was first recorded in 1930, in the Broadway musical Lew Leslie’s International Revue starring Harry Richman and Gertrude Lawrence. Richman first recorded ‘On the Sunny Side of the Street’ in 1930 and a recording by the Ted Lewis Orchestra released the same year came close to topping the Hit Parade.
“Other hit versions were recorded by Lionel Hampton (1938), Jo Stafford & the Pied Pipers (1944), and Tommy Dorsey & the Sentimentalists (1945).”