"Didn't We Almost Have It All" is the second single from Whitney Houston's second album Whitney, and was nominated for Song of the Year at the 1988 Grammy Awards. The song was written by Michael Masser and Will Jennings and was released in August 1987. 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.

The single was number one on the US Billboard Hot 100 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 a Saratoga Springs, New York date.

"Didn't We Almost Have It All" reached number one on the Billboard Hot 100 for two weeks, from September 26 to October 9, 1987, where the song became her fifth consecutive number one. The song also topped both component charts, the Hot 100 Single Sales and Hot 100 Airplay, Houston's fourth song (and fourth consecutive release) to do so.

The single stayed in the Top 40 for thirteen weeks, and topped the Billboard Adult Contemporary Charts for three weeks.

Internationally, the song hit the top ten in several markets, and reached the Top Twenty in the United Kingdom (#14); Switzerland (#18); and Germany (#20).

"Didn't We Almost Have It All" was ranked twenty-second on the Billboard Hot 100 year-end charts (1987), and remained in the Billboard Hot 100 for seventeen weeks. It was her fifth number one single on the Billboard Hot 100, her fourth on the Billboard Hot 100 Single Sales, her fourth on the Billboard Hot 100 Airplay, and her fifth on the Billboard Adult Contemporary Charts.

The season 3 finale of Grey's Anatomyand an episode of the eighth season of Degrassi: The Next Generationare named after this song.

It is widely speculated the song is about Houston's relationship with then NFL star Randall Cunningham.

The Austrian singer Lia Weller performed the song in the fourth season of the talent show Starmania. Although it was generally considered one of the best performances of the evening, she was voted off. A week later, she released the Song on iTunes.