The first time I heard Francis Albert Sinatra was as a young kid. My parents would play his music and I’ve loved him ever since. There’s something to his range of energy that is so captivating. One minute, he could sound down on his luck, singing songs about the one that got away.

The next, he’s full of bravado and confidence, as he swaggers through a tribute to one of his many favorite towns. Many of his songs were originally written for other singers or Broadway shows, but his covers have been so iconic that the songs are considered his.

Saturday, December 12^th would have been Sinatra’s 100^th birthday. He may have left us 17 years ago, but his legacy and persona still live on. In honor of Sinatras’ centennial, here are my top five (no order) songs of the Chairman of the Board.

Luck Be A Lady

Originally a show tune from the musical “Guys and Dolls”, Sinatra adopted it as a signature piece in 1963. once a fast paced ensemble number, Sinatra transformed it into a slower, big band piece. Sinatra lectures Lady Luck, who he thinks is about to run out on him. He begs her to stay by his side and not leave him through the night. The song has been used in movies (Mrs. Doubtfire) and TV shows (Family Guy).

It Was a Very Good Year

This Grammy award winning song of 1966 was originally for Bob Shane and the Kingston Trio. This song is Sinatra looking back at the women he’s banged over the years. Whether he was screwing small town girls on the village green (17 years old) or boning blue bloods in the back of limousines (35 years old), Sinatra was certainly a ladies’ man. And this song shows it.

Only The Lonely

One of Sinatra’s many torch songs (sentimental love songs about lost love), “Only The Lonely” sings about how everything he knows and everything he does is based off his loneliness. His dreams, the places he goes, the songs he sings: all remind him of the lost love he has. He spends the song recalling his loss, and ending with a plea to hang on to love. Otherwise, you will be singing this song like him

Theme From New York, New York

What was once a Liza Minelli number for a Martin Scorsese movie has become an anthem for the greatest city in the world. Played at the end of Yankee games and New York Ranger games, Sinatra croons about a bright city with endless possibilities. He praises New York as the gold standard, proclaiming, “If I can make it there, I’ll make it anywhere.”

My Way

One of Sinatra’s greatest hits. Written by singer Paul Anka over the melody of French song “Comme d'habitude”, “My Way” has Sinatra reflecting about life and the path he took. He talks about how hard it was and how it was worth it because it was all the better because he did it “his way.” The song has been covered by artists like Elvis and Sid Vicious.

Happy 100th Birthday, Ol’ Blue Eyes.