Well i had iTunes on random today and came across "Have a Cigar" by Pink Floyd. Which Got me thinking, how many songs are there about smoking cigars?
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There's that cigar arson song by Brad Paisley that about once or twice a year, someone posts the story of as a "completely true, I swear, my friend emailed it to me, he'd never lie" story.
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Johnny Cash mentions "and smoking big cigars". Lots of rappers rap about cigars too.
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A star lit up like a cigar
Strung out like a guitar
Maybe you could educate my mind
Explain all these controls
I can't sing but I've got soul
The goal is elevation.

- U2
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From 9's barettas and moving raw
To chillin in wine cellars sticks in humidors
That's what I call mature

-nas

Stearns
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I forget what song it was, but my father was telling me about a song where the singer says "A Sherman in my hand". He never knew he was referring to a Nat Sherman cigar until a few months back.

Google'd it and it was Peter Frampton.

"Champaign for breakfast and a sherman in my hand" Peter Frampton
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Nat Sherman is also a huge manufacturer of cigarettes. I would guess Frampton was likely referring to a cigarette. :-)
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True. Though you don't usually smoke a cigarette with Champagne. Though I suppose you could, I think cigars are more appropriate for occasions you have where you drink champagne. I forget where he read it but I believe it was an interview where he was talking about the inspiration of the song.

EDIT:
From what I read, the song it comes from seems to be from the lifestyle of the rich and famous. So I would think it would refer to the cigars as opposed to cigarettes. When you think of people smoking cigars in the media it is either someone who is badass, or rich.
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http://www.25smokinfigurados.com/
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Frampton is referring to a dipper, which is also called a Sherman. Has nothing to do with a cigar. LOL

Jethro Tull's Aqualung mentions "As he bends to pick a dog end". I was told dog end was British slang for a cigar nub.

Roger Miller in King of the Road says "I smoke old stogies I have found".

Boston in the song Rock and Roll Band sings "Smoking big cigars, drove in cadillac cars".
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Jethro Tull - "A Small Cigar"

Cream - "N.S.U."
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