It’s not far-fetched to suggest that Frank Sinatra probably didn’t have many things he regretted about his artistic career, despite his ups and downs in his personal life.

Often called the ‘Chairman of the Board’; He’s a huge icon in popular culture. With around 150 million records sold, he’s one of the world’s top-selling artists, which really highlights his massive influence.

Sinatra was born in Hoboken, New Jersey, and his life was like a roller coaster in the world of music, filled with both incredible highs and crushing lows. He had famous friends, well-known romances, and many extraordinary experiences that most regular folks can only dream of. There were even rumors of connections to the mafia.

Given how well he lived his life, it’s safe to say he didn’t make too many mistakes.

For good reasons, many believe that Sinatra was a dedicated student of music. Oddly enough, he didn’t really study much, adding to his complex personality. But his natural talent and charm were off the charts, propelling him to unprecedented heights. He provided the soundtrack as America was becoming a global superpower.

Interestingly, despite not putting in a ton of effort into practicing, Sinatra managed to release an impressive 59 studio albums over his 54-year career.

He was incredibly prolific, putting out a whopping 297 singles. Such a feat is extremely hard to match in the world of popular music. Some of his famous hits include ‘New York, New York,’ ‘That’s Life,’ ‘Fly Me to the Moon,’ and ‘I’ve Got the World on a String.’ These songs played a major role in shaping popular culture and solidifying Sinatra as a 20th-century hero.

He was a key figure in the swing era. Frank went from performing in New York clubs to headlining in Las Vegas. He showcased a remarkable rise in American music history. Later, it even became a model for performers like Elvis Presley.

Everyone knows Sinatra’s name; with his name written as one of the major figures in entertainment due to his musical contributions.

But it’s interesting that he had a strong dislike for one classic song; and his opinions could spark some debate.

Frank Sinatra absolutely despised the 1966 number one hit ‘Strangers in the Night’ and wasn’t shy about expressing it. He’d even tell fans who requested the song at his shows that he couldn’t stand it. He’d reluctantly introduce the song by saying, “Here’s a song that I cannot stand.”

Now, why did Sinatra have such a strong aversion to this song? In a biography from 2006 titled “Sinatra: The Life” by Anthony Summers and Robbyn Swan, it’s noted that he actually called the song “a piece of shit” and “the worst fucking song that I have ever heard.” Shockingly, he also made some homophobic comments about the song, suggesting it sounded like it was about “two fucks who meet in the bus station bathroom.”

Yet, despite these controversial views, the song became his first number-one hit in 11 years.

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