Today would’ve marked Ol’ Blue Eyes’ 101st birthday so what better way to honor him than going through his catalog.

Favorite Song: Fly Me to the Moon

I’ve thought long and hard about this, but ultimately I continue to land on this as my all-time favorite Sinatra song. Many others are close behind though.

Song Deserving of More Popularity: Chicago

Not many people know this song, as they are more familiar with “My Kind of Town”. But I would argue this is the better song about the Windy City. I am biased though, because I lip-synced this song back in 7th grade for a Spring musical at my school. Killed it.

Best Car Sing-Along Song: That’s Life

Got pulled over once for speeding while this song was blaring from my radio (no ticket, just a warning). Couldn’t help it, the song just gives you a lead foot and makes you want to scream it at the top of your lungs.

Song That Makes You Want to Sip Whiskey: One For My Baby

Four ice cubes, two fingers of Jack Daniel’s whiskey, a splash of water and this song playing.

Best Live Song: TIE! The Lady Is A Tramp/I’ve Got You Under My Skin

Not sure where this one is from, but a comment says it was at a comeback concert at Madison Square Garden in 1974, so we’ll go with that.

This is from Sinatra At The Sands which has some of the absolute best versions of his music.

Best Song That Didn’t Need Skatting: Strangers In The Night

This could be one of his best, but for me, I could really do without the skatting at the end. Song is pretty perfect other than that.

Best Duet: Me & My Shadow with Sammy Davis, Jr.

Best Song With a Girl’s Name in the Title: Emily

He actually has a fair amount on songs that mention girls by name (this, Nancy (With the Laughing Face), Sweet Lorraine, Tina), but this is the best one of those.

Best Song Used in The Sopranos: It Was A Very Good Year

Season 2. Episode 1.

Best Christmas Song: Have Yourself A Merry Little Christmas

No question about it.

Most Bad-Ass Photo of Sinatra: 

Coolest Photo of the Rat Pack:

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