1. Traumatic Birth

Born on December 12, 1915, in a Hoboken, New Jersey, apartment, Francis Albert Sinatra was blue and not breathing when he was yanked out of his mother with forceps. Thought to be dead, the infant was laid on the kitchen counter while the doctor attended to his mother. His grandma picked up the newborn, stuck him under some cold water, and little Frank wailed out his first song.

2. Physical Insecurities

Those forceps left their mark on the left side of Sinatra's face, in the shape of a scar that ran from the corner of his mouth to his jaw line and a cauliflower ear. As a teenager, he was nicknamed "Scarface." He also suffered a bad case of adolescent acne, which left his cheeks pitted. Self-conscious about his looks as an adult, Sinatra often applied makeup to hide the scars. Even with that, he hated to be photographed on his left side. The physical insecurities didn't end there. Sinatra also wore elevator shoes to boost his five-seven stature up a few inches.

3. Bad Boy Image

Sinatra's bad boy image began with his infamous 1938 mug shot. The charge? At a nightclub, one of his girlfriends attacked his wife-to-be Nancy and later had Frank arrested twice – once for seduction and again for adultery.

4. Manufactured Hype

In the 1940s, Frank – or Frankie, as he was then known – became one of America's first teen idols. Not to take anything away from his amazing voice and his ability to excite the female throngs, but the bobbysoxer craze he incited (so called because the coed fans wore Catholic school-style bobby socks, rolled down to their ankles) had a little help. Sinatra's publicist George Evans auditioned girls for how loud they could scream, then paid them five bucks and placed them strategically in the audience to help whip up excitement.

5. The House I Live In

In 1945, Sinatra made a short film, The House I Live In, that spoke out against anti-Semitism and racial intolerance. Ironically, a decade later, its liberal slant got him tagged as a Communist sympathizer during the McCarthy trials. Sinatra never testified, but it was more fodder for his already growing FBI file.

6. FBI File

That FBI file had been started by J. Edgar Hoover a few years later after a radio listener wrote to the Bureau, saying, "The other day I turned on a Frank Sinatra program and I thought how easy it would be for certain-minded manufacturers to create another Hitler here in America through the influence of mass hysteria." Sinatra had also been investigated by the FBI for reportedly paying doctors $40,000 to declare him unfit to serve in the armed services.

7. Introduction of Concept Album & Box Set

In 1946, Sinatra's debut release, The Voice of Frank Sinatra, helped introduce both the concept album and the box set. At a time when long-playing records were still novel, Sinatra issued a set of 78 rpm records with eight songs, all with a theme of lost love. It sold for a hefty $2.50 (the equivalent of about $30 today). But the price didn't prevent it from topping the charts for seven weeks. Two years later, it became one of the first-ever pop music vinyl 10" LPs. Sinatra would later make classic concept albums like Only The Lonely and In The Wee Small Hours for Capitol Records.

8. Suicide Attempts

Frank's star fell hard in the early 1950s. He was so low that he even attempted suicide. Walking through Times Square, he saw mobs of girls waiting to get into a concert by new singing sensation Eddie Fisher. Feeling washed up, Sinatra went back to his apartment, put his head on the stove, and turned on the gas. Luckily, his manager found him in time, lying on the floor, sobbing. Sinatra made three other suicide attempts, all of them in the throes of his volatile relationship with actress Ava Gardner.

9. The Summit

With his pals Dean Martin, Sammy Davis, Jr., Joey Bishop, and Peter Lawford, Sinatra led the Vegas clique known as the Rat Pack. The name was coined by actress Lauren Bacall years earlier to describe a Hollywood drinking circle that included her then-husband Humphrey Bogart and Sinatra. The guys in the Rat Pack actually referred to themselves by a different name – The Summit – playing on a 1960 summit meeting in Paris between top world leaders.

10. Signature Drink

James Bond has his martinis, shaken not stirred. And for Ol' Blue Eyes, the cocktail of choice was a mix of four ice cubes, two fingers of Jack Daniel's whiskey, and a splash of water. "This is a gentlemen's drink," he once said. And if you want to hold the drink like Frank, don't touch the rim. Cup it in your hand, insulated by a cocktail napkin.

11. New York, New York

Sinatra actually had two hits called "New York, New York." The first was in 1949, from the film On the Town, and was written by Leonard Bernstein, Adolph Green, and Betty Comden. Thirty years later, Sinatra cut "(Theme From) New York, New York," by John Kander and Fred Ebb. Originally from Martin Scorsese's 1977 bomb New York, New York, Sinatra turned it into his signature song and onstage closer. He also angered the lyricist, Ebb, by customizing the words (Sinatra had done this to a few songwriters, most famously Cole Porter), adding the climactic phrase "A-number-one." In 1993, Sinatra recorded the song again, this time as a duet with Tony Bennett.