In 1932 Paul Whiteman and His Orchestra with vocalist Jack Fulton were the first to make the pop charts with their recording of “How Deep Is the Ocean?”

The song would spawn four hit recordings that year:

• Paul Whiteman and His Orchestra (Jack Fulton, vocal, #5)
• Guy Lombardo and His Royal Canadians (Carmen Lombardo, vocal, #4)
• Rudy Vallee and His Connecticut Yankees (Rudy Vallee, vocal, #7)
• Ethel Merman (with Nat Shilkret and His Orchestra, #14)

In 1945, with Peggy Lee’s growing appeal, Columbia released a 1941 recording:

• Benny Goodman and His Orchestra (Peggy Lee, vocal, #19)

Preceding the Great Stock Market Crash of 1929, life for Irving Berlin had been both productive and profitable. His life, however, was not without its troubles. In 1928 Berlin’s three-week-old son died, precipitating a bout of depression that would last for several years. Also, in the latter half of the 1920’s, Berlin had let up on what had been non-stop songwriting and began to doubt his viability as a composer. In Caryl Brahms and Ned Sherrin’s book Song by Song: The Lives and Work of 14 Great Lyric Writers, Berlin confesses, “I was scared ...I had had all the money I wanted for the rest of my life. Then all of a sudden I didn’t. I had taken it easy and gone soft, and wasn’t too certain I could get going again.”

Discouraging experiences with early Hollywood musicals gave Berlin further reason to despair, and while he continued to write songs he lacked the self-confidence to promote them.

In 1932 when the rest of the country was sunk in the depths of the Great Depression, Irving Berlin embarked on the second half of his career. Unwilling to accept Berlin’s professional demise, Max Winslow, a friend and employee, retrieved a song Berlin had filed and presented it to Rudy Vallee. “Say It Isn’t So” became a number one hit and one of only a few Berlin songs to be introduced on the radio. The song endures to this day as a jazz standard.

A reenergized Berlin then borrowed four lines of the chorus of his “To My Mammy” (1920), including the querying phrase, “How Deep Is the Ocean?” and created a new song whose lyrics are a succession of questions, “How deep is the ocean? (How high is the sky?)”

How much do I love you?
I’ll tell you no lie.

The second line, “I’ll tell you no lie,” is the only line that does not ask a question. Philip Furia, in The Poets of Tin Pan Alley: A History of America’s Great Lyricists depicts the lyrics as

Another slang formula--the Yiddish penchant for answering a question with another question...