Bad boys and faithless women populated blues and country songs for decades.  Broadway musicals have had their share, from the lovable petty crooks of Guys and Dolls through the switchblade gangs of West Side Story to the tiny crooks of Bugsy Malone and serial killer Sweeney Todd.
So, whittling my choices down to just five has not been easy but I tried to go for the unexpected.
1.       EVERY BREATH YOU TAKE
written and performed by Sting/Police
Sting’s anthem for stalkers remains a song of choice for wedding couples.  Do they actually listen to the lyrics?  Sting wrote it not in the throes of love but in the throes of possessive jealousy when his first marriage had just ended.  “Every breath you take, every move you make, I’ll be watching you” is essentially a bunny boiler alert.  This is a guy you want to take a restraining order out on, not walk up the aisle with.
2. PSYCHO KILLER
written and performed by David Byrne/Talking Heads
The person described in this early hit for Talking Heads, the hip band of the late seventies and eighties, isn’t the cold, emotionless psychopathic type we’re now familiar with.  This psycho killer can’t sleep because his bed’s on fire and you’d better not touch him because his nerves are inflamed too.  But it doesn’t matter that the psychological profile doesn’t fit  – lead singer/songwriter David Byrne with those unblinking eyes staring out of his bony face is plenty scary, thank you very much.

3. VAMPIRES

written and performed by Paul Simon
Unlikely as it sounds from the “Bridge Over Troubled Water” guy, Paul Simon was already into minor criminal activity with his first solo album.  When he and his friend Julio were down by the schoolyard they were smoking dope. With the stage show/album “The Capeman” he graduated to murder and, in fairness, rehabilitation.  This fifties-set study of a Puerto Rican teen gang, the Vampires, co-written by Nobel Prize poet Derek Walcott, knocks West Side Story into a cocked hat.
The highlight of this particular song is an account of a fight between a skinny Puerto Rican and a big Irish kid “who looks like a ton of cold beef floating in beer.”  I met Walcott once and, hoping to ingratiate myself with him, I gushed about how the word choice, the rhymes and the rhythm made this a truly powerful piece.  (All of which is true.) He dismissed me with the words: “Paul wrote that one.

4.       POTTER’S FIELD

written and performed by Tom Waits
Tom Waits is the other poet laureate of America’s underbelly and many of his early songs were inspired by a combination of film noir, Edward Hopper paintings and Charles Borkowski-like barflies.   His “Invitation To The Blues” is essentially the first act of The Postman Always Rings Twice; his “Burma Shave” is Thieves Like Us.
“Small Change”, the title track of his second album, doesn’t mess around.  Its first line is: “Small Change got rained on with his own .38.”  His account of the young punk who got into an altercation by a jukebox is a short story masterclass in song.  Much later, with “Trouble’s Braids”, on the album “Swordfishtrombones”, he spends about 90 seconds brilliantly describing the experiences of a wounded man on the run evading his pursuers before the man floats down a creek out of the song.
However, the one I like best is from his third album, “Foreign Affairs”.  “Potter’s Field” is a story told by a stool pigeon who would “double cross his mother if it’s whiskey that they paid”.
His nickname is Nickel and he knows where a guy is hiding out who stole half a million dollars in unmarked bills.  The story is elliptical – the guy slept last night in a wheelbarrow “with only revenge to keep him warm” (and a siren for a lullaby)- but he also paid “a king’s ransom for a bedspread” sometime or other.  And he may well be dead.  If you want to find this fugitive, Nickel suggests you seek out Captain Charon, who sails from the Bronx across the River Styx.  Wonderful stuff.  I suspect Pelecanos and Lehane long ago listened and learned.
 5.            MACK THE KNIFE
written by Kurt Weill and Bertolt Brecht
No list would be complete without arch-criminal MacHeath from The Threepenny Opera.  This guy is so cool he can even survive T S Eliot turning him into Macavity the mystery cat (and Andrew Lloyd Webber consequently turning him into a character in Cats).   Bad, bad Leroy Brown, with his 32 gun and a razor in his shoe ain’t got nothing on Mack the Knife.
The song has been wrecked by so many (shame on Frank Sinatra) but I first heard the blowsy Bobby Darin version – it was one of the first 45 rpm singles I bought.  On the label “Bertolt” is “Bert” and I assumed Bert and Kurt was just another Tin Pan Alley/Brill Building writing duo.  In the eighties, “Lost In The Stars”, a great collection of Kurt Weill songs sung by the rock royalty du jour, has Sting (who played MacHeath on Broadway) and Dominic Muldowney doing a great version of the song.  Oh, the shark has pretty teeth, dear – and he shows ‘em pearly white.  You betcha.
Peter Guttridge
Peter Guttridge was born in Burnley, a cotton-weaving town in Northern England. He was brought up in the shadow of Pendle Hill where four hundred years ago the Lancashire Witches lived, turned their neighbours into toads, and died. He spent a year studying history at Oxford University before the authorities sussed him and threw him out. He finished his degree at Nottingham University and, ten years later, a second degree in film studies at London University.
Guttridge spent much of his twenties traveling and doing a range of jobs—from kitchen porter to barman, shop assistant to sewerage worker—while trying to write fiction. He traveled in America for six months and ended up in Santa Cruz, California, where for a year he tried to write “The Great Novel.” He failed. On his return to London, England, he wrote a comic piece about his woeful experiences attempting to busk in New Orleans when he could neither sing nor play guitar. A British magazine accepted it and his career as a journalist began.
For the next three years this same magazine sent him each month to experience a dizzying range of activities: from going on a tour of Scandinavia with a rock band to performing as a male stripper in London’s Soho. While he still had some shred of dignity left he moved across to the quality British newspapers—The Times, The Guardian, The Telegraph, The Observer, and The Sunday Times—where for the next ten years he wrote about music, film, literature, and the comedy industry.