Joel's follow-up effort to 1973's Piano Man, Streetlife Serenade did not enjoy the relative success of its predecessor; it marked the beginning of his frosty relationship with critics and the music industry more generally. In "The Entertainer", Joel mocks the entertainment industry, reminiscing over his record label's earlier insistence that the single version of Piano Man's title track (the album's major hit) be shortened to maximize radio airplay:
"It was a beautiful song but it ran too long./If you're gonna have a hit, you gotta make it fit./So they cut it down to 3:05."
"The Entertainer" peaked at #34 on the US Singles Chart. The album itself peaked at #35 on the charts, eventually selling over one million copies.
The album contains two songs that were featured in many of Joel's live shows during the 1970s: the instrumental "Root Beer Rag" and the short song "Souvenir", which Joel often played as the final encore during that time period. Two others, "Streetlife Serenader" and "Los Angelenos," were included on Joel's first live album, Songs in the Attic (1981).