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Today, Frank Sinatra would’ve been 100 years old. Perhaps more than any other artist, his career perfectly summed up the 20th century. He began singing professionally in 1935, and released his first record in 1939. He caused a pandemonium later paralleled by Elvis, The Beatles, and Michael Jackson all the way back in the ’40s, single-handedly made middle-agedom cool in the ’50s and ’60s, retired and came back in the ’70s, entered the ’80s with hit records, and released his multi-platinum selling final album in 1994. From music to movies to style to politics, if you look back over the last century, you’re likely to find Sinatra somewhere in the mix. He wouldn’t have wanted it any other way.






And while his music is still beloved by millions, its his lifestyle that still continues to equally fascinate us. Simply put, he’s an icon — one who stayed at the top of his game for decades and continues to be the benchmark of how we measure class. For years, he was the wealthiest entertainer in the world, doing something that seems impossible today: Living in a way that people aspired to, not mocked. It’s no accident that Jay-Z compares himself to the man – 100 years on, he’s still the gold standard.
And like his style and attention to detail, Sinatra’s eye was extended to his cars. He loved them, and they were usually both stylish and perfectly of their times. So to celebrate the man’s birthday, we went digging and found 10 of the most important rides to ever reside in Frank Sinatra’s garage, from his first car to the last.