5 Shocking Facts You Didn't Know About Frank Sinatra

On December 12, 1915, Singer Frank Sinatra was born in Hoboken, New Jersey. He later became one of the most influential singers of the 20th century. Here are 5 shocking facts about the singer nicknamed “Ol’ Blue Eyes.”


His Nickname as a Teen Was Scarface Forceps were used in Sinatra's birth, leaving a scar from his jawline to his mouth, along with a cauliflower ear. His nickname was “Scarface,” when he was a teen, and to add more problems, he suffered from severe acne that pitted his cheeks. Sinatra hated being photographed along his left side and often used makeup in an attempt to hide his scars. His physical insecurities didn’t end there. At 5’7, he also wore elevated shoes to appear taller.

He Was Arrested For Seduction And Adultery Frank Sinatra’s brief stint in lockup was thanks to his womanizing ways. In 1938, the crooner was dragged into jail on the charge of seduction, evidently a serious deal back in the ’30s. Sinatra was caught sleeping with an upstanding single woman, a pillar in the community until she was corrupted by Frankie’s wicked ways.The charge was eventually dismissed, and Sinatra was let go until he was hauled back to the slammer the following month. After doing a little detective work, authorities discovered Sinatra’s lady friend was married, and Frank was charged with adultery. Eventually, officials dropped the case, and after a combined total of 16 hours in jail, Sinatra was back on the prowl.


He Tried to Commit Suicide Numerous Times Sinatra was a heavy drinker and described himself as manic-depressive, or bipolar. During the 1950s, he tried to kill himself with a gas stove because he thought his popularity was waning. Fortunately, his manager found him in time to save his life. While he was with Ava Gardner, he tried to commit suicide three times, once by trying to shoot himself.

Sinatra Could Have Played the Lead in Die Hard The role of John McClane ended up going to Bruce Willis in the movie Die Hard, but Sinatra had first call on the part. This is because the movie was based on a sequel to the book “Nothing Lasts Forever” called The Detective in which Sinatra had starred back in 1968. Because Sinatra was 73 at the time Die Hard was being cast, it was probably a good idea that he turned the role down.

The FBI Had a Big Investigative File on Sinatra Without a doubt, “My Way” is Frank Sinatra’s most iconic song. It become his trademark song and audiences wouldn’t let him end a show without singing about how he’d lived his life without regrets. The song became a part of music history, and soon everyone was singing it, not just Sinatra. “My Way” has been covered by everyone from Sid Vicious to the Three Tenors. In 2005, it was played at more British funerals than any other pop song. The funny thing about all of this is that Sinatra absolutely hated “My Way.” And whenever he performed live, he told audiences exactly what he thought about it. During a gig at Caesars Palace, he told the crowd, “I hate this song—you sing it for eight years, you would hate it too.” But the fans wanted “My Way” so he gave it to them without fail.