"On the Sunny Side of the Street" (1930) is a song with music composed by Jimmy McHugh and lyrics by Dorothy Fields, which 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 Ted Lewis, Dave Brubeck, Earl Hines, Louis Armstrong, Benny Goodman, Lionel Hampton, Errol Garner, Dizzy Gillespie, Art Tatum and Count Basie.[1]
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 in 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 The Manhattan Transfer, Dinah Washington, Ella Fitzgerald, Judy Garland, 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. The children's group Sharon Lois and Bram recorded a version for their 1990 hit Sing A to Z recording, as well as performed the number on their critically acclaimed hit television series Sharon, Lois & Bram's Elephant Show. It appeared on the last episode of Season 4 in 1987 titled "Band on the Run". Dizzy Gillespie, Sonny Rollins, and Sonny Stitt recorded their well-known version on their 1957 album Sonny Side Up.
In 1959 Keely Smith recorded it with Billy May and his Orchestra for her Capitol LP, Politely!
On March 20, 1961 Frank Sinatra recorded it with Billy May and his Orchestra for his Capitol LP, Come Swing With Me.
The Coasters also recorded a version of this song.
Willie Nelson included a cover of the song on Stardust, his 1978 album of jazz and popular standards.
Steve Allen in his mystery novel, The Talk Show Murders (1982), suggested that the song refers to "passing" — the possibility of light-skinned blacks passing for white.
About 1966, Gene Kelly recorded a cover version with slightly altered lyrics:
Around 1990, John Paul Larkin, or Scatman John, also did a rendition of this song.
In 1994, Barry Manilow covered the song for his album, Singin' With The Big Bands, a recording which featured The Tommy Dorsey Orchestra.
In 1995, a version of the song performed by Steve Tyrell was included on the Father of the Bride Part II soundtrack (UPN # 8-0927-45475-2-1)
In 2003, Cyndi Lauper recorded a zydeco-flavored cover of this song on her standards/covers album At Last.
In 2007, Zooey Deschanel sings the song for Stephen Berra's movie The Good Life
In 2008, The Manhattan Transfer did a close harmony version of the song for the CD/DVD 35th Anniversary - The Great American Songbook
In 2010, Canadian singer Nikki Yanofsky recorded a mash-up version of this song with Led Zeppelin's "Fool in the Rain". It is a bonus track on her debut studio album Nikki.
In 2010, Rod Stewart recorded the song for his Fly Me to the Moon... The Great American Songbook Volume V cover album.
At the 2011 edition of the Rochester Jazz Festival, Trombone Shorty played the song for a packed, free concert.
Also, Face To Face covered it. The song with the same title by the The Pogues, however, is not a cover of this song, it's an original Pogues composition[2].