Why Frank Sinatra Hated Singing ‘Strangers in the Night’

What was the last great Frank Sinatra album? It’s a good question for Sinatra fans and critics alike. Even the harshest views of his career acknowledge the greatness of the Columbia (1946-50) and Capitol (1954-62) years. And, “My Way” and other songs notwithstanding, most agree the Chairman of the Board fell off (as most artists do) in his late (Reprise) years.

Wherever you land on that, there’s no argument about how the music-buying public’s tastes changed in the ’60s. That was when, with The Beatles rolling, Sinatra landed his final solo No. 1 with “Strangers in the Night.” While the public couldn’t get enough of that ’66 hit, Sinatra hated the song from the start. And his opinion of it worsened over time.

Frank Sinatra thought ‘Strangers in the Night’ was an awful song

Closeup of Sinatra from the waist up holding a microphone and singing into it in 1976
1976: Frank Sinatra (1915-98) sings at a benefit concert. | Daniel Rosenblum/Keystone/Getty Images

According to the account in Sinatra: The Life, “Strangers in the Night” never got any love from the man who made the song famous. “I don’t want to sing this,” the authors quote Sinatra telling Irving Weiss the first time he saw the music. “It’s a piece of s–t.”

In later years, Sinatra took to trashing the song whenever he had the chance. After performing “Strangers” in concert one night, a microphone caught him saying (via The Life), “That’s the worst f–king song I ever heard.”

If that doesn’t settle it, fans can check on the fan site The Frank Sinatra. There, site operators were kind enough to compile a list of times Sinatra savaged the song on microphone while standing on stage.

“Yeah, here’s a song that I can not stand,” Sinatra said at a ’75 Jerusalem gig. “I just cannot stand this song, but what the hell.” The list goes on and on. The gist is the same: He wanted to puke almost every time he sang it. But he did it anyway.

Sinatra ground his teeth and kept singing ‘Strangers in the Night’

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Why would Sinatra keep singing a song he hated? He didn’t do anything he didn’t want. (It was “Frank’s world,” etc. etc.) Well, in brief, the song had been his last huge hit — much bigger, upon release, than “My Way” — and Sinatra knew it had kept him near the top. On stage, he would say “Strangers in the Night” had “kept him in pizza” for years.

In other words, it paid for his helicopter fuel, landscaping additions in Palm Springs, and so forth. After the ’60s, the song helped pack arenas of adoring (and paying) fans. He wasn’t going to disappoint them, so he ground his teeth and sang it. At times (as in the above performance), his contempt for the song was palpable.

Sinatra turned on ‘My Way’ late in his career

“Strangers in the Night” wasn’t only late hit Sinatra didn’t appreciate. By the ’80s, he began disparaging “My Way” as well. The difference was, Sinatra loved that song when he first heard it. Paul Anka, who wrote it especially for Sinatra, never doubted that.

It took Sinatra years — after hearing it and singing it hundreds of times — for him to turn on “My Way.” With “Strangers in the Night,” it was a case of “hate at first listen.” And you can’t blame Sinatra one bit. When Frank was right, he was right.