Playlist: Rock Songs About… Outlaws, Desperados & Other Various Criminals

*Photo of William H. Bonney, aka “Billy The Kid,” taken from Wikipedia, credited to Bill Wittick, circa 1880 and probably copyrighted

I’m not sure why, but lately I’ve taken to saying to the Rock Chick, “You’ve always been an outlaw.” Perhaps some context is in order. I usually say this to her when I’m riding in the car with her. Since I’m a big fan of whiskey, it makes sense that she should take the wheel. Don’t drink and drive out there, kids.

I’m not sure she’s ever heard the words “defensive driver.” It’s like riding with those guys in the Dukes Of Hazard or Starsky… or maybe Hutch, I get them confused. The rules of the road are mere guidelines for that woman. I’m surprised we’ve never been airborne.

Once, when I thought she was going to be pulled over at a speed trap, I said, “Hand over your jewels, I can’t afford to go to jail, I’ve got a meeting tomorrow.” This of course got me labeled as a “square.” It left me wondering if I’d be come “the Man”?

I couldn’t get away with anything as a youth so I steered back to the other side of the line. My lawful way of living doesn’t mean I don’t have a healthy disrespect for authority and authority figures. I’ve never reacted well to being under anybody’s boot. I’ve always felt we should question everything. Of course, that still doesn’t make me an outlaw.

Since I’ve been repeating it a lot lately, it got me thinking about outlaws. According to Wikipedia (and Websters) an outlaw is defined as “a person declared as outside the protection of the law.” Webster also goes on to describe it as, “A lawless person or a fugitive from the law.” Sounds about right.

My thoughts on outlaws (and desperados) really got supercharged when I was listening to the new box set from the Eagles, One Of These Nights (Deluxe). It includes a concert from 1975. At the show they play a ton of songs from the 1973 album, Desperado. I can’t tell you how many outlaw tracks are on that record. A playlist began to crystallize.

Many of the songs I started this list off with were about the old Western type of outlaws like Billy The Kid (pictured above) or Jesse James. But pretty soon I had songs about more contemporary criminals and desperados.

Of course as Don Henley sang, “A man with a brief case can steal more money than any man with a gun can.” Considering the amount of corruption in the U.S. right now, it appears lawlessness is currently “the coin of the realm” in my country.

Now, on this list I tried to confine it to outlaws. There’s no Hendrix “Hey Joe” or Robert Cray “Smoking Gun” because I felt like those were crimes of passion. A woman did them wrong so they shot ’em. It’s not cool but it doesn’t make you an outlaw.

There are a ton of songs about serial killers out there – “Murder By Numbers” (the Police), “Midnight Rambler” (the Stones), even the story of the cannibalistic “Dirty Frank” (Pearl Jam). But again, I didn’t feel like that collection of killers were outlaws. It felt like a deeper pathology was at work there.

I was stunned at the number of songs about prostitutes out there. I consider prostitutes to be victims, as we’ve certainly learned about the horrible things the Epstein Class has been up to, not outlaws. I never understood music guys focus on “ladies of the night” since, as Dire Straits sang, rock stars “get their money for nothing and their chicks for free.” Maybe musicians work the same hours… it’s a proximity thing?

There are naturally a lot of songs about drug smugglers and dealers. Bands writing about drugs? Who’d have figured? I wonder what that connection is? Musicians… And of course there were family rumors that grandpa ran a little moonshine back in the day so perhaps I too have the same affinity for smugglers?

There were a couple of outlaw “vibe” kind of tracks like Van Halen’s “Mean Streets” or GnR’s “Welcome To The Jungle,” but those tunes seemed rather broad for my purposes. There certainly seemed to be a lot of criminals hanging around in those songs though… And remember “A gun is real easy in this desperate part of town.”

I tried to find repeat offenders. Guys who’d broken the law and were fugitives. Sure, we’ve got tunes about the aforementioned old West bad guys – the James Gang, the Dalton Gang, and Billy the Kid – but I tried to expand the list beyond those ol’ cowboy desperados. We have thieves and a couple of murderers. I also included some tracks about prisoners because obviously, they’ve broken the law.

And while this list is nothing like what Obi Wan Kenobi said, “You will never find a more wretched hive of scum and villainy,” it’s got a lot of bad guys. Although, I have to admit, there is something I’ve always admired about the outlaw spirit.

Perhaps it’s the freedom. It’s how I can root for Michael Corleone in The Godfather. Maybe it’s the whole myth of the Robin Hood thing but there are some outlaws in the songs on the list I’d hang out with. And let’s be honest, in an insanely corrupt world, maybe only the good men are outlaws now.

Here are my 80 favorites. These are the songs I could come up with off the top of my head. If you’ve got a favorite song about a desperado or an outlaw, please put it in the comments and I’ll add it to the dreaded Spotify playlist.

Our goal is always to turn you on to a song you haven’t heard or perhaps haven’t heard in a while. I advise a small tumbler of dark and murky fluid with these tunes. Maybe pull the cork out with your teeth, pretend you’re Cole Younger. My thoughts on the tunes are below.

• Bob Dylan, “Outlaw Blues” – Great blues rock anthem for outlaws! Somehow we end up in Australia, but it’s Dylan so it’s ok.
• Bruce Springsteen, “Murder Incorporated” – Isn’t this the Mafia’s nickname?
• AC/DC, “Jailbreak” – I almost think the escaped criminal in this song is the only good guy in the story? And of course “He made it out…with a bullet in his back.”
• Social Distortion, “Partners In Crime” – I like to think this the Rock Chick and my approach to life. From their great new album, Born To Kill. 
• Styx, “Renegade” – “Lawman has put an end to my runnin’.” Great Tommy Shaw penned rocker. Styx kind of sold out in the 80s but we loved them in the late 70s.
• Mudcrutch, “Bootleg Flyer” – The first of many drug smuggling songs.
• Slash featuring Chris Robinson, “The Pusher” – It’s a Steppenwolf song but I couldn’t resist a cover with Slash on guitar and the Black Crowes Chris Robinson at the mic. From Slash’s Orgy Of The Damned. 
• Warren Zevon, “Desperadoes Under The Eaves” – Finally a desperado shows up!
• Iggy Pop, “Neighborhood Threat” – Bowie covered this later. “Did you see his eyes? Did you see his crazy eyes?”
• Eagles, “Outlaw Man” –  I probably could have included the whole Desperado LP.
• David Crosby, “Rodriguez For The Night” – Haven’t we all lost a “chick” to an outlaw? Bad boys, what are you gonna do ladies?
• AC/DC, “Dirty Deeds Done Dirty Cheap” – Only the Bon Scott led AC/DC could write an advertising jingle for a hitman/enforcer that actually rocks.
• The Faces, “Borstal Boys” – A shoutout to our juvenile offenders, past and present.
• Tom Petty & The Heartbreakers, “Something Big” – There’s always a small time hood working an angle or looking for the big score.
• Steve Earle, “Copperhead Road” – Smuggling tale that ends with a Vietnam Vet smuggling pot.
• Bruce Springsteen, “Outlaw Pete” – Ok, this is just a silly song, but we’ll always back Springsteen.
• Bob Dylan, “Billy 1” – Dylan’s great track about Billy The Kid.
• Fiona Apple, “Criminal” – I’m not sure, but once upon a time, I may have dated the character Fiona sings about here.
• Alice Cooper, “Desperado” – Another wonderful track about a desperado.
• John Mellencamp, “Authority Song” – Ah, the theme of my youth. While I fought authority, I rarely won.
• Sammy Hagar, “I Can’t Drive 55” – Dedicated to the Rock Chick and her lead foot.
• Warren Zevon, “Frank And Jesse James” – Another great Zevon track, written originally for the Everly Brothers who rejected it.
• Eagles, “Doolin-Dalton” – Another cowboy, outlaw gang song.
• Tom Petty & The Heartbreakers, “Spike” – “Look out, another one, just like the other ones, Another bad-ass, another troublemaker…” This song used to be huge in Wichita.
• Sam Cooke, “Chain Gang” – I can’t help but feel sorry for the men on the chain gang. Cruel and unusual, indeed.
• The Traveling Wilburys, “Tweeter And The Monkey Man” – Dylan doing a send up of Springsteen. I think every character is a bad guy except maybe “sister Jan.”
• The Stooges, “Search And Destroy” – “I am a world’s forgotten boy, The one who searches and destroys…” Young, violent, and wired.
• Paul McCartney & Wings, “Band On The Run” – The story of the prison escape by a band who somehow ran afoul of a sheriff. Maybe they played some Barry Manilow?
• Bob Marley & The Wailers, “I Shot The Sheriff” – To be clear, the sheriff is the criminal in this song. Like the singer, I don’t know anything about the deputy.
• The Clash, “Police And Thieves” – Are they both bad guys here?
• Tom Petty & The Heartbreakers, “Don’t Pull Me Over” – Another story of somebody with a carload of some kind of narcotic with is fingers crossed the cops don’t pull him over. Featured on our Playlist: Rockers Doing Reggae. 
• Graham Nash, “Prison Song” – Nash lamenting the two tiered justice system in the U.S. where folks selling dime-bags go to jail for years and rich folks can’t be found in jail.
• Bruce Springsteen, “Harry’s Place” – This track always gave me Sopranos vibes. One thing is for sure, Harry is not a man to fuck around with.
• Jane’s Addiction, “Been Caught Stealing” – The kleptomaniac anthem!
• Elton John, “Have Mercy On The Criminal” – One of those instances where someone, in this case the criminal, is trying to make a deal with his Lord for a little help in escaping.
• The Clash, “I Fought The Law” – “And the law won…” This is why I was never an outlaw.
• John Lee Hooker, “I’m Bad Like Jesse James” – Johnny Lee Hooker slow rolling a blues number…he was bad like Jesse James.
• Supertramp, “Crime Of The Century” – Supertramp in 1974 singing about the crime of destroying the environment.
• Stephen Stills (Manassas), “Love Gangster” – Menacing song from a jealous boyfriend.
• Elvis Presley, “Jailhouse Rock” – Warden throws a party for the various criminals in his jailhouse, including the Purple Gang.
• Led Zeppelin, “Gallows Pole” – An outlaw on the gallows who is saved from his fate by his outlaw sister. Must run in the family.
• Wolfmother, “Joker & The Thief” – Clearly the thief is an outlaw, but the Joker sounds super sketchy as well.
• Keith Richards, “Nothing On Me” – The ultimate outlaw troubadour claiming not that he’s innocent, but that “they’ve got nothing on me.”
• Social Distortion, “Like An Outlaw (For You)” – Prison Bound is a fabulous early Social D album everyone should hear.
• Bad Company, “Bad Company” – “Company, always on the run, Destiny is the rising sun…”
• Joni Mitchell, “Raised On Robbery” – Prostitutes are victims not outlaws, but this is such a great song I had to include it.
• Social Distortion, “Lawless” – Social D describing the current U.S. administration.
• David Bowie, “Criminal World” – Great deep track from Bowie featuring Stevie Ray Vaughan on guitar.
• Judas Priest, “Breaking The Law” – Economic circumstances drove the narrator to well, break the law for some excitement. Widespread poverty is a policy choice.
• The Temptations, “Papa Was A Rolling Stone” – Papa certainly did have a lot of fun, though.
• J. Geils Band, “Funky Judge” – This song just makes me laugh. Peter Wolf’s scream when the verdict comes down is worth the price of admission.
• Allman Brothers Band, “Midnight Rider” – Great song about an outlaw on the run.
• Elton John, “Ballad Of A Well Known Gun” – Old Western story about a gunslinger brought to justice.
• The Cult, “Outlaw” – Absolute unhinged rock n roll.
• Tom Petty & The Heartbreakers, “The Criminal Kind” – Another song about a sketchy woman.
• Warren Zevon, “The Long Arm Of The Law” – Song about a lifelong outlaw… like Zevon himself in a way.
• Randy Newman, “Little Criminals” – Another tale of petty criminals trying to put together a big score. In this case, robbing a gas station.
• Eddie Money, “Gimme Some Water” – “I was the one who got good with the gun…” At least his brother is there when they hung him.
• Bon Jovi, “Wanted Dead Or Alive” – Great outlaw anthem.
• Eagles, “Desperado” – Ladies, there’s not a man you’ve dated/married who hasn’t at one time in his life heard this song on a car radio and thought, “Yeah, that’s me.”
• Johnny Cash, “Folsom Prison Blues” – “I shot a man in Reno just to watch him die.” How could I not include this song?
• Thin Lizzy, “Waiting For An Alibi” – Valentino, a gambler, may be cheating some people.
• Steve Miller Band, “Take The Money And Run” – Young couple turns to crime. But like Javert, Billy Mack a detective from Texas, is on their trail.
• Warren Zevon, “Mr. Bad Example” – Don’t live your lives like this children. He really is a bad example.
• Macy Gray, “I’ve Committed Murder” – There was enough premeditation in this murder that I had to include it. Her first album always made me smile.
• The Clash, “Police On My Back” – The Clash certainly seem to have a lot of trouble with the cops.
• Bruce Springsteen, “Meeting Across The River” – Small time hood signs up for a “job” in the city, but doesn’t have a car.
• David Crosby, “Cowboy Movie” – Epic story of train robbers nabbed by an undercover lady cop.
• Steely Dan, “Don’t Take Me Alive” – Great criminal fugitive song. “Got a case of dynamite, I could hold out here all night…”
• Mike Ness, “Dope Fiend Blues” – Drug addicts really need treatment not jail, but this is a harrowing tale from the back of a police car. I had to include it.
• Thin Lizzy, “Jailbreak” – I always do chuckle at the line, “There’s gonna be a jailbreak, somewhere in this town…” I’m pretty sure it’s at the jail.
• Lucinda Williams with Elvis Costello, “Jailhouse Tears” – Lucinda and Elvis make a very entertaining duet couple.
• Steely Dan, “Kid Charlemagne” – “Don’t you know you’re still an outlaw in their eyes?” Famous drug dealer stayed at the party too long.
• Bruce Springsteen, “The Ballad Of Jesse James” – Early, obscure Springsteen in the days before E Street. “Don’t you wanna be an outlaw?”
• Van Halen, “D.O.A.” – I don’t know what David Lee Roth and his gang is up to, but the sheriff is not happy about it. And how did “they found a dirty faced kid in a garbage can” go down?
• Social Distortion, “Prison Bound” – Another great outlaw track, which is like, the third song from this album.
• Glenn Frey, “Smuggler’s Blues” – Another smuggler lament. “You be cool for 20 hours and I’ll pay you 20 grand.” Hmmm, ok.
• Jeff Beck Group, “Hangman’s Knee” – Another song about bargaining with the hangman… with Jeff Beck‘s heavy lead guitar and Rod Stewart’s bluesy vocal. Ronnie Wood on bass!
• Red Hot Chili Peppers, “Police Station” – Lead singer Anthony Kiedis wrote this song after seeing some old “acquaintances” from his drug days on a police poster. It might have been a lover? Sad song anyway you slice it…with a gorgeous vocal.
• Bruce Springsteen, “Stolen Car” – I decided to end on this stark track from The River. A man whose marriage has gone bad turns to crime, driving stolen cars, hoping to get caught. “Each night I wait to get caught but I never do.” Maybe just get a divorce?

There you have it. Again, the playlist is not meant to be exhaustive, just entertaining. Who hasn’t been fascinated by a Robin Hood character in the past. There’s something wild and free about outlaws… well, when they’re not committing crimes. If you’ve got a suggestion for an additional track, drop it in the comments.

And remember what I said, in a rogue state, the only true outlaws are the good men. Think… John Brown of Kansas from the Civil War. Not that I’m advocating any type of violence here. I’m more of a “civil disobedience” guy.

Enjoy this at maximum volume… maybe scare the neighbors… it’s what an outlaw would do.

Cheers!