Crime bosses are known for being cruel and violent, but they can also often be funny. Below are some of the wittiest and funniest quotes by Tony Soprano from his most comical moments in the show.

Livia Soprano: Well, all I know is, daughters are better at taking care of their mothers than sons.
Tony Soprano: Yeah, and I bought CDs for a broken record.Tony Soprano, S1.Ep1: Pilot

Christopher Moltisanti: What about the dead guy?
Tony Soprano: You keep prodding him with a stick. You light a candle to Saint Anthony. But I think you’re f***ed.Tony Soprano, S1.Ep2: 46 Long


Being a rebel in my family would have been selling patio furniture on Route 22.Tony Soprano, S1.Ep5: College

I’m f***ing King Midas in reverse, here. Everything I touch turns to s***.Tony Soprano, (to Jennifer), S1.Ep12: Isabella

Uncle Jun and I, we had our problems with the business. But I never should have asked him about eating p***y. This whole war could have been averted. Cunnilingus and psychiatry brought us to this.Tony Soprano, S1.Ep13: I Dream of Jeannie Cusamano

Jennifer Melfi: I have patients who are suicidal.
Tony Soprano: Well, they’re not gonna feel any better about their life if you get clipped.Tony Soprano, S1.Ep13: I Dream of Jeannie Cusamano

Artie Bucco: Look me in the eye. Tell me you didn’t lay a finger on my place!
Tony Soprano: I didn’t burn down your restaurant. I swear on my mother.Tony Soprano, S1.Ep13: I Dream of Jeannie Cusamano
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Ten years you thought about Janice? There are men in the can better looking than my sister.Tony Soprano, (to Richie), S2.Ep5: Big Girls Don't Cry

When you’re married, you’ll understand the importance of fresh produce.Tony Soprano, (to Christopher), S2.Ep7: D-Girl

A.J. Soprano: It’s in my history book.
Tony Soprano: So, you finally read a book and it’s bulls***.Tony Soprano, S4.Ep3: Christopher


What do you get when you cross an accountant with a giant jet airplane? A Boring 747.Tony Soprano, S5.Ep4: All Happy Families

Fran Felstein: I was sorry to hear about your mother.
Tony Soprano: At least she didn’t suffer. She made all of us suffer, instead.Tony Soprano, S5.Ep7: In Camelot

Tony Soprano: You know what they say, “Revenge is like serving cold cuts.”
Jennifer Melfi: I think it’s, “Revenge is a dish best served cold.”
Tony Soprano: So, what’d I say?Tony Soprano, S5.Ep10: Cold Cuts
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