“Darn That Dream” was introduced in the Broadway musical, Swingin’ the Dream, which opened November 29, 1939, at the Center Theater. The show closed shortly thereafter, on December 9^th, after only thirteen performances. Lack of talent was not its downfall. Among those who sang “Darn That Dream” in the production were Louis Armstrong (as Bottom, pictured above), Maxine Sullivan (as Tatiana, Queen of the Pixies), Bill Bailey, Dorothy Dandridge, Vivian Dandridge, and Etta Jones, the latter three billing themselves as the Dandridge sisters (as three pixies.)

The show’s short run was a disappointment for all involved, especially the investors who lost nearly $100,000, one of the costliest failures of the time. For Benny Goodman, however, there was a residual bright spot. At the end of January “Darn That Dream,” featuring vocalist Mildred Bailey, became his first of three Top Ten pop-chart hits of 1940. “Darn That Dream” hit the charts two more times that year,

• Benny Goodman and His Orchestra (1940, Mildred Bailey, vocal, #1)
• Blue Barron and His Orchestra (1940, Russ Carlyle, vocal, #14)
• Tommy Dorsey and His Orchestra (1940, Anita Boyer, vocal, #16)

Besides “Darn That Dream,” Jimmy Van Heusen and Eddie De Lange wrote five other songs for Swingin’ the Dream: “Swingin’ a Dream,” “Moonland,” “Peace, Brother,” “There’s Gotta Be a Weddin’,” and “Spring Song.” Benny Goodman shares credit for the music on the latter song. “Love’s a Riddle” also appeared in the show and was written by Alec Wilder, with Van Heusen and De Lange sharing credit for the lyrics. “Darn That Dream” would be the only hit from the score.

Based on A Midsummer Night’s Dream and billed as a “musical comedy extravaganza,” Swingin’ the Dream was set in New Orleans in 1890. The cast of 150, mostly African American actors, singers, and musicians, included, besides those mentioned above, Ruth Ford, Dorothy McGuire, Jackie “Moms” Babley, Butterfly McQueen, the Benny Goodman Sextet, Bud Freeman and His Summa Cum Laude Orchestra, and a full orchestra conducted by Don Voorhees. Agnes DeMille choreographed the dance numbers and Walt Disney did the artwork for the sets.

Swingin’ the Dream was panned by audiences and critics alike. The morning after opening night Brooks Atkinson of the New York Times said,

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.

In 1998, the title Swingin’ the Dream was recycled for the book, Swingin’ the Dream: Big Band Jazz and the Rebirth of American Culture by Lewis A. Erenberg. The book is unrelated to the play but makes an interesting case that the Big Band Era, 1935-1948, was as relevant as the subsequent Bebop era, the former being when American popular music rid itself of the constraints of European influence. Erenberg discusses how the collaboration of African Americans and second-generation immigrants changed American culture and society.

In his book, American Popular Song: The Great Innovators, 1900-1950, Alec Wilder notes hundreds of jazz standards but in the case of “Darn That Dream” injects a bit of personal history. Asked to write an entire score for Swingin’ the Dream, which he did, Wilder then had to take it back “due to the duplicitous character of the producer.” For one reason or another, his composition “Love’s a Riddle” was kept in the show. Wilder comments that when he met Van Heusen, he was inclined to dislike him because of the circumstances. Regardless of his feelings at that time, Wilder shows a genuine appreciation for Van Heusen’s music, devoting to him nearly ten pages of mostly complimentary text in his chapter titled “The Great Craftsmen.”