“Didn’t We Almost Have It All“ is the second single from Whitney Houston‘s second album Whitney. The song was written by Michael Masser and Will Jennings and was released in August 1987. It received a Grammy nomination for Song of the Year.
Originally, another song was to be released as the second single, “For the Love of You,” but Arista Records decided to release “Didn’t We Almost Have It All” instead because all Houston’s singles had to be original material at this point of her career.
The single was number one for two weeks on the US Billboard Hot 100 chart even though there was not a video for the song. A live performance of the song recorded during Houston’s successful 1987–1988 Moment of Truth World Tour was played on MTV, VH1, and BET. The performance is from her September 2, 1987 concert in Saratoga Springs, New York. The recorded performance was also televised along with her performance of “I Wanna Dance With Somebody” at the 1987 MTV Video Music Awards on September 11. It was widely speculated that the song is about Houston’s relationship with then NFL star Randall Cunningham.