Songfacts®:

• "Darn that Dream" appeared on the album Birth of the Cool in 1957, which showcased pivotal recordings made between 1949 and 1950 by Miles Davis' nonet. This recording clearly demarcated Davis' transition from Bebop to "Cool Jazz," in which he attempted to make Jazz accessible again to the listening public after Bebop had digressed into unintelligibility throughout the 1940s.
• "Darn that Dream" is considered to be one of the more daringly experimental popular tunes of its generation, using a chromatic harmony and complex arrangement. This particular song shows the inclusion of a distinctly popular music idiom with its roots in classical polyphony, cementing Davis' departure from the Bebop genre. His solo near the end of the song is a work of supreme understatement, coolly simplistic.
• This song tells the story of a disappointed lover who repeatedly dreams that his lost love will return his affections, even though he knows that this will never happen. He desperately holds on to this sad state because it is the only way he can be with this lover: "Darn that dream and bless it too. Without that dream, I never would have you."
• This song is a popular Jazz standard that appeared in a Broadway production entitled Swingin' the Dream, which was a collaboration between the popular music composer James Van Heusen and band-leader and lyricist Eddy De Lange written in 1939. The original show incorporated artwork and sets by Walt Disney, music by the Benny Goodman Sextet, and an extravagant cast of 150 people. Despite the lavish production, Swingin' the Dream was notoriously unpopular and was canceled after only 13 performances – one of the biggest and most expensive failures on Broadway of its time.
  
  The plot of Swingin' the Dream was based on Shakespeare's A Midsummer Night's Dream, but this did not play to its strengths, of which the music was chief. The New York Times said of the opening night that "it would have been better to throw Shakespeare out of the window. Every now and then a flare of dancing breaks through the professorial patter, and the Benny Goodman boys perform brilliantly on a piece of music. But the going is heavy through the long stretches of the evening."
• Unlike the show in which it featured, "Darn that Dream" has had a very long shelf-life. After the initial Broadway performance by Louis Armstrong in 1940, this song became a standard sung by the likes of Ella Fitzgerald (on Ella Swings Gently with Nelson in 1962), Billie Holiday (on All or Nothing at All in 1996) and Doris Day (on You're My Thrill/Young at Heart in 2007). The music has also been performed by notables other than Miles Davis and Benny Goodman, such as Thelonious Monk and Ahmad Jamal.
• On Birth of the Cool, "Darn that Dream" features the vocals of Kenny Hagood, who had been a vocalist in the Bebop scene throughout the 1940s, singing for the Dizzy Gillespie Orchestra before recording this song with Miles Davis in the 1950s.