“Knowing When to Leave” (Jill O’Hara/Dionne Warwick/Dusty Springfield)

“Knowing When to Leave” by Jill O’Hara from the original Broadway production of Promises, Promises

Today’s classic song of the day is “Knowing When to Leave,” from the Broadway musical, Promises, Promises. Like all the rest of the tunes from the play, this one was written by Burt Bacharach and Hal David. (Burt did the music, as usual, and Hal did the words.)

Promises, Promises is a musical adaptation of director Billy Wilder’s 1960 film, The Apartment, which starred Jack Lemmon, Shirley MacLaine, and Fred MacMurray. The plot involves a junior executive at an insurance company who lends his apartment out to upper managers, who use it for their afternoon and evening trysts. In the film, Jack Lemmon played the junior exec, Fred MacMurray played his boss, and Shirley MacLaine played their mutual love interest.

Jerry Orbach and Jill O’Hara in the original Broadway production of Promises, Promises

It took a few years, but Bacharach, David, and writer Neil Simon got together to turn The Apartment into a musical. That musical, titled Promises, Promises, opened on Broadway on December 1, 1968, with Jerry Orbach in the Jack Lemmon part, Edward Winter as the lascivious boss, and Jill O’Hara as their girl. Michael Bennett did the choreography, which was magnificent. (Just take a peek at the batshit crazy dancing in the “Turkey Lurkey Time” number; it is insanely over the top.) Promises, Promises ran for 1,281 performances and was nominated for seven Tony Awards, winning two—Best Performance by a Leading Actor in a Musical (for Jerry Orbach) and Best Performance by a Featured Actress in Musical (for Marian Mercer).

“Turkey Lurkey Time” by the original Broadway cast of Promises Promises

In the play, Miss Kublick, played by Jill O’Hara, sang “Knowing When to Leave” when she decides to end her relationship with Mr. Sheldrake, the big boss. It was intended to be a showstopper and the musical’s bit hit song; it was certainly the former, although it was “I’ll Never Fall in Love Again” that became the big mainstream hit from the play.

“Knowing When to Leave” is a terrific tune. The words, and there are a lot of them, tumble out in a stream of rushing emotion. The music is big and brassy and the vocal line is twisty enough to challenge even the most talented of singers. Then there are the high notes, which push most vocalists to the very top of their ranges. This should have been a mainstream hit; I don’t know why it wasn’t.

Not surprisingly, many singers glommed onto “Knowing When to Leave” as a big showstopper number for their live acts—and several released versions of the song before the musical even opened. As near as I can tell, the first recording of “Knowing When to Leave” was by a little-known singer named Sue Raney. Other early recordings of the song were released by Michelle Lee, Kelly Garrett, Lyn Roman, Bambi McCormick, Betty Buckley, and, in an instrumental version, the Baja Marimba Band. (Burt Bacharach released his own instrumental version of the song in May of 1969.)

“Knowing When to Leave,” by Sue Raney

Probably the best-known recording of “Knowing When to Leave” was made by Bacharach/David favorite Dionne Warwick, which appeared on her 1970 album, I’ll Never Fall in Love Again. It made sense for Ms. Warwick to record this one, due to her string of hits from the Bacharach/David team, including a top ten hit from Promises, Promises, the album’s title track.

“Knowing When to Leave” by Dionne Warwick

In 2010, a revival of Promises, Promises appeared on Broadway, running for 291 performances. This version starred Sean Hayes as the Jerry Orbach character and Kristin Chenowith in the Jill O’Hara part. As you might suspect, “Knowing When to Leave” was a big showstopper for Ms. Chenowith.

“Knowing When to Leave” by Kristin Chenowith from the 2010 Broadway revival of Promises, Promises

My personal favorite version, however, was by Dusty Springfield, who never recorded it but performed it live on the TV special, Another Evening with Burt Bacharach, which aired on the the NBC network on September 13, 1970. (It was actually part of the Kraft Music Hall series.) Dusty pulls out all the stops on this one, keeping up with the rapid-fire lyrics that go by at a breakneck pace and capping it off with the bravura final high note. I think Dusty gave Dionne strong competition as the best interpreter of those sophisticated and difficult-to-sing Bacharach/David songs.

“Knowing When to Leave” by Dusty Springfield from the 1970 TV special, Another Evening with Burt Bacharach
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