Didn’t We Almost Have It All

The song Didn’t We Almost Have It All was born from a decision that changed the course of Whitney Houston's second album. While recording in Los Angeles, her label Arista Records had planned to release a cover of For the Love of You by Isley Brothers as the second single, but ultimately chose something different: an original ballad that is now a classic. The lyrics, written by Will Jennings and composed by Michael Masser, speak of that moment when two people were on the verge of achieving something great together, but something went wrong. It is not just a song about lost love, but about the nostalgia for what could have been and never was.

The composition process took longer than usual. According to Jennings, he and Masser worked on the song for years, with endless calls from a hotel in Nashville that added up to over two hundred dollars in expenses. The final version was recorded in 1986 at studios like Devonshire and Sigma Sound, with Houston involved in the vocal arrangements. When it was released in July 1987 as part of the album Whitney, it became her fifth consecutive number one on the Billboard Hot 100, matching legends like Elvis Presley and The Supremes. It was also nominated for Song of the Year at the Grammy Awards in 1988, cementing its place as one of the most remembered ballads of the 80s.