Former Mob Boss Ranks The Greatest Mob Songs Of All Time

Frank Sinatra. Dean Martin. Tony Bennett. Everybody thinks they know what the mob listened to because they saw Goodfellas. People, I didn’t watch the life in a movie theater. I lived it. I sat in those clubs. I was at those weddings. I stood in line at the Copa with my father. And some of the men who sang these songs were around our world — everybody knew it.

So today I’m doing something I’ve never done: 18 songs, four tiers, S down to C. I’m not ranking who sang it best. I’m ranking how fast it puts me back at that table. Some of these put me right back in the room. Some of them — and you’re not going to like this — Hollywood snuck onto the playlist.

Sinatra, Dino, Darin, Prima, the Four Seasons, the Stones, Clapton — and the one song the whole country sang along to without noticing it’s about a gangster.

And stick around to the end, because I go off the list and tell you about a song that had nothing to do with the mob — the one I heard in a prison cell that told me I was going home.

Tell me what I got wrong. Tell me what I left off. I read them.

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0:00 What the Mob Really Listened To

1:50 How the Tier Rankings Work

2:50 Growing Up at the Copacabana

5:35 Frank Sinatra: My Way

8:24 Luck Be a Lady & Mob-Era Vegas

9:11 That’s Life