Sunny Side of the Street may refer to:

"Sunny Side of the Street" (song), a 1990 song by The Pogues Sunny Side of the Street (Bryn Haworth album), a 1975 album Sunny Side of the Street (film), a 1951 comedy film directed by Richard Quine The Sunny Side of the Street, a 2006 John Lithgow album The Sunny Side of the Street (film), a 2022 film directed by Lau Kok-rui Sunny Side of the Street, a painting by Philip Evergood "On the Sunny Side of the Street", a 1930 song and jazz standard written by Jimmy McHugh and Dorothy Fields