I was sad to read in the New York Times the other day of the death of songwriter Ervin Drake, at the age of 95. When I was embarking on The B-Side, one of the first people I walked to was Michael Feinstein, the songwriter, pianist, and drum-beater for the Great American Songbook. He gave me Mr. Drake’s phone number and said I should interview him, as the last living link to the pre-War Tin Pan Alley era of songwriting.

Good advice. When I called the number, a woman answered; she turned out to be Mrs. Drake, the former Edie Bein, and she turned out to be in charge of his schedule and affairs. In short order I arranged to drive out to the Drake home in Great Neck, Long Island, for a conversation. It was a good talk. He ranged over this long career as a songwriter, television producer, and advocate for songwriters. Here is some of what I wrote:

Songwriter Ervin Drake—born Ervin Maurice Druckman in New York in 1919—had been drawn to the trade in part by his older brother Milton, who’d had some success on Tin Pan Alley, notably with “The Java Jive,” a hit for the Ink Spots in 1940. He got his big break as a result of the radio networks’ 1941 ban of songs by writers affiliated with the venerable licensing group ASCAP. Ralph Peer, a country-oriented publisher who was affiliated with a competing organization, BMI, asked Drake to write lyrics for a traditional Brazilian song called “Tico Tico no Fuba.” The Andrews Sisters charted with the tune in 1944. He developed a specialty in providing English to words South American melodies, including “Yo Te Amo Mucho (And That’s That),” which Xavier Cugat played in a movie called “Holiday in Mexico,” and “You Can in Yucatan,” performed by Desi Arnaz. Also in 1944, Drake wrote the lyrics for Duke Ellington’s instrumental “Perdido.” Between the successes, there was a lot of hustling. “I put in nights sitting in places that were part restaurant, part dance halls,” he recalled. “I’d try to get next to the bandleader and give him a song of my own.”

In contrast to many Tin Pan Alley songwriters, Drake had a social conscience. In 1943, in reaction to the racial and religious segregation practiced by hotels and restaurants, he wrote a tune he called “No Restricted Signs in Heaven.” He took the song to a new recording label, Capitol Records, which had been started just a year before by two songwriters, Johnny Mercer and Buddy De Sylva, and Glen Wallichs, a record-store owner.

“I didn’t want it to seem like a message song so I did it with a boogie-woogie tempo,” Drake said of “No Restricted Signs” in a 1996 interview. “Johnny wanted to record it. He showed it to his partner, and Glen said, ‘John, the way things are in this country if you record that song we will lose our distributorship.’” So Capitol passed, but the musician and producer Enoch Light ended up taking the song to a gospel group called the Golden Gate Quartet, who released their version in 1946.

The biggest hit of Drake’s early career, by contrast, would be unplayable today because it is almost entirely made up of crude racial stereotypes. Lying in the bathtub one day, as he recalls, the song came to him in its entirety: a novelty number called “Rickety Rickshaw Man,” whose lyrics begin “There’s a coolie name o’ Chulee/Runs a rickety rickshaw south of Peking/He goes a clippety-clop-clop/Clippety-clop-clop/As he hobbles down the cobble-stoned street.” Ralph Peer persuaded a sweet bandleader Eddy Howard to record the song, which reached number 6 on the Billboard charts in 1946.

As usual, Drake careered from the ridiculous to the sublime, this time drawing from his own life. He had been dating a showgirl named Edith Bein and felt deeply in love with her. But she began to be courted by “all these Wall Street types,” Drake told Will Friedwald in 2009. “I felt like I couldn’t compete, so I just withdrew from her life.” In the midst of the subsequent depression, he heard a haunting melody by Irene Higginbotham. “It hit me — smack!” he said in the Friedwald interview. “This is exactly what I felt when Edith left me. So in about 20 minutes I wrote the whole lyric to ‘Good Morning Heartache.’” A couple of months later, Billie Holiday made an immortal recording of the song, and it has since become a blues standard.

When I sat and talked to Drake in his Great Neck, New York, home in 2010, sitting in on the conversation was his wife. It was none other than the former Edith Bein. The two had reunited in 1975, after their respective spouses had died.

Drake would go on to co-write the inspirational credo “I Believe” and, on his own, the songs for a Broadway adaptation of What Makes Sammy Run?, which included the swinging “A Room Without Windows.” In 1961, he wrote an elegaic ballad for The Kingston Trio. Four years later, Frank Sinatra heard it on his car radio driving to Palm Springs, California; his recording won him a Grammy award and was a staple of his concerts from that point on. The song? “It Was a Very Good Year.”