"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. A live performance from her September 2, 1987 concert in Saratoga Springs, New York was used as the official video and played on MTV, VH1, and BET. 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.

Rob Wynn of Allmusic highlighted the song. L.A. Times editor Robert Hilburn wrote: "Houston's stardom will be boosted most by "Didn't We Almost Have It All," a sweeping Masser-Will Jennings ballad with the kind of big, emotional finish that will make Liza and hundreds of other singers wish they had been given first crack at the song. I'll save my champagne for pop singers who don't add that overblown song to their repertoire." Rolling Stone's Vince Alleti wrote: "Masser reprises the show-tune schmaltz of "The Greatest Love of All" in his even cornier "Didn't We Almost Have It All." According to Whitney fanpage: "But there is a cut on the album whose title inadvertently sums up Houston at this stage of her development -- "Didn't We Almost Have It All." St. Petersburg Times editors Eric Snider and Annelise Wamsley described "Didn't We Almost Have It All" as "an overblown tune co-written by Michael Masser (...) that finds Houston stripped of subtlety - with her wire-to-wire belting, you can just see the fetching songstress looking skyward, arms outstretched." Following Houston's death in 2012, Entertainment Weekly published a list of her 25 best songs and ranked "Didn't We Almost Have it All" at 16.

...
Wikipedia