“Tom Dooley”, though he was more a coward.
Everyone knows about song “Beauty and the Beast” sung by Angela Lansbury, but the boys like me watching that film wants to drink like “Garcon!”
Irving Berlin has one in ANNIE GET YOUR GUN, it’s even called “I’m a Bad, Bad Man!”
“Knew a girl in Omaha,
But I ran faster than her Pa!
Cain’t go back t’ Omaha, I’m a bad bad man!”
OK, it’s not the highlight of the show.
Randy Newman has a bunch–‘There’s a Party at My House Tonight’ goes on about the fun and a pretty girl who’s invited, and in the last two lines it becomes apparent he intends to rape her. ‘In Germany Before the War’ is about a real-life serial killer his mother told him about. ‘Guilty’ and ‘Marie’ are about men who know they’re bad, but are trying to be nice. And of course, his musical version of FAUST has tons of great songs for Lucifer, the uber-bad boy.
The collected works of Tom Waits and Nick Cave.
While somebody already mentionedn Don’t Mess Around with Jim, I humbly submit its superiority among bad men songs by being about two very badass men.
First Big Jim Walker, a “pool shootin’ son of a gun”, who’s “big and dumb as a man can come and strong as a country hoss”, and furthermore, “when the bad folks all get together at night you know they all call Big Jim boss”.
However, comes along a pool-shootin’ boy name of Willie McCoy, who evidently got hustled by Big Jim, and he “come to get [his] money back”. The carnage is such that “when the cuttin’ was done the only part that wasn’t bloody was the soles of the big man’s feet”, and Slim replaces Jim on top of the badass ladder.
The moral, of course, is not to hustle people strange to you, even if you do have a two-piece custom pool cue. Indeed.
How about some Shane McGowan-era Pogues?
The Old Main Drag
“One evening as I was lying down in Leicester Square
I was picked up by the coppers and kicked in the balls
Between the metal doors at Vine Street I was beaten and mauled
And they ruined my good looks for the old main drag”
The Sickbed of Cuchulainn
“And in the Euston Tavern you screamed it was your shout
But they wouldn’t give you service so you kicked the windows out
They took you out into the street and kicked you in the brains
So you walked back in through a bolted door and did it all again”
Knowing Mr McG’s reputation for liking a wee tipple, I think his lyrics aren’t just an affectation, either.
No it’s a good question: Zee-Zee Top 99% of the time is the answer. (The other 1% is people pretending to be unknowledgeable, for a joke)
“Voodoo Child (Slight Return)” by Hendrix or Stevie Ray Vaughan, though I lean toward Hendrix.
First verse is pretty much the dictionary definition of “badass.”
On a lighter note, “Smokin’ In The Boys’ Room” - the Brownsville Station version, if there’s a choice.
Since Shel Silverstein’s already been mentioned, how about Tiger Man McCool ?
I thought of another one this morning on my way to work…John O’Reilly by Charlie Robison. It is about an Irish immigrant who becomes a boxer in the U.S.
“Well I fought in New York City and I fought the Jersey Shore,
My gut stayed full of whiskey and my bed stayed full of whores,
My right they called a cannonball and my left they called the same,
and I left 'em all a’lying half in blood and half in shame.”
I think you mean Gaston. But I agree.
Surprised nobody’s mentioned Guns N’ Roses yet.
I used to love her
But I had to kill her
I used to love her
But I had to kill her
I had to put her
Six feet under
And I can still hear her complain
Shaft!!!
man… sometimes I wonder about you guys.
Also,
Cop Killer - Body Count
Walk Like A Man (despite the decidedly non-badass falsetto singing) - The Four Seasons
Get a Little Dirt on Your Hands - Bill Anderson
Beat me to it. I LOVE that song. Old Sam got caught and he’s on the scaffold:
You could tell this was a man who knew he had nothing left and he was going to go out swinging. Finest kind.
Eminem’s “'97 Bonnie & Clyde” about a guy who takes his daughter along to dump her mother into the lake:
I picked up Tori Amos’ version of this. She sings it slow and clear, and hearing it over the speakers late at night at home scared the p*** out of me. If you can forget that it’s Marshall Mather and treat it as if he was channeling Poe – after all, how different is this from “A Cask of Amontillado” or “The Tell-Tale Heart”? – and I think you may understand where I’m coming from.
I’m surprised that no one has brought up the relative motherlode of bad-assness: gangsta rap. How about these examples?
From NWA’s “F*** tha Police”…
"Lights start flashin behind me
But they’re scared of a n**** so they mace me to blind me
But that shit don’t work, I just laugh
Because it gives em a hint not to step in my path
…
Smoke any muthaf***a that sweats me
Or any assho that threatens me
I’m a sniper with a hell of a scope
Takin out a cop or two, they can’t cope with me"
Or, how about this from Tha Dogg Pound’s “I’ma Gangsta”
“You thought you had a grip, well we did too
That’s why me and the homies decided to come through
Whip out the pistol, snatch off his head real quick
Bitch n****, where the f*** did you stash the grip
On some gangsta sh** 'cause gangstas make the world go ‘round
Whip out the fo’ pound, dump 'cause he’s moving around
I bet he never move again, the next time a motherf***er say stay down
On the ground, I bet he won’t make a sound”
Okay, maybe nobody posted this stuff because of all the censoring for a non-Pit thread. Whew…
But you have to admit, they are (verbally, at least) some badass m&#@f%#$!
Yeah, we all know that that Shaft is a bad mutha (SHUT YO MOUTH!) but “Theme From Shaft” spends waaaay more time talking about what a lover and sex machine he is.
It’s borderline. Deserves an honorable mention, along with “Theme From Fall Guy” and “Theme From Dukes Of Hazzard.”
EVERYBODY NOW! “Makin’ their waaaaaAAAAAaaaaay the only way they know hooOoooooow…!”
Yeah, gangsta rap! Gheto Boys - Mind Playing Tricks On Me – didn’t I mention this in the OP?
Oops, sorry! My bad!! 
Geto Boys - I *loved * their featured song in Office Space… “Damn It Feels Good to Be a Gangsta”… Just perfect. They are pretty bad-ass too!
How about Behind Blue Eyes by The Who. Not loud and boastful, but rather chilling in it’s own way…