When Smokey Sings

The first single from Alphabet City is a tribute to the singer Smokey Robinson in both title and lyric. It reached 11 on the UK singles chart and five on the Billboard Hot 100, ABC's second American top 10 hit. Together with its B-side Chicago it topped the Billboard dance club chart. In the week ending 3 October 1987, ABC's single and Robinson's One Heartbeat were in the Hot 100 top 10 at the same time. Richard Niles arranged the strings.

The bass line is an homage to Robinson's 1970 hit with the Miracles, The Tears of a Clown. Robinson said that was a form of flattery and he really appreciated it. The album and single versions differ in the bridge: the album version names Luther, Sly, James and Marvin, while the single replaces them with other lyrics followed by a short saxophone solo. Barry McIlheney of Smash Hits was unimpressed, writing that it was not half as good as any of their older stuff. Dave Simpson of the Guardian listed it among the hits of the first set when the band played Birmingham in 2019.