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“As through this world you travel, you'll meet some funny men; Some will rob you with a six-gun, and some with a fountain pen.”  So begins Woodie Guthrie’s 1939 The Ballad of Pretty Boy Floyd. Ma Joad, in John Steinbeck’s The Grapes of Wrath, suggests that Pretty Boy Floyd was a victim – motivated by a punishing Depression and the madness and meanness of those around him, he fell into a life of crime more by necessity than inherent evil.  “I believe you've killed me, so you can go rot in hell” said Channing Tatum to his assumed killer Melvin Purvis as Pretty Boy Floyd in 2009’s Public Enemies.  

From music to literature to film, references to Pretty Boy Floyd have truly pervaded pop culture.  For some reason, maybe his name, maybe his handsome face, maybe his notorious history or an American fascination with crime and mystery, Floyd is one of the most infamous of the tommy-gun era gangsters. Although Floyd was a cold, hard criminal - Public Enemy No. 1 after the death of Dillinger - he was generally perceived as a “good guy” by the 1930’s populace.

On October 22, 1934, Floyd was shot in a corn field behind a house in Ohio. According to Wikipedia, “varying accounts exist as to who shot him and the manner in which he was killed. He was carried out of the field by FBI agents and died under an apple tree.” Even in death, Floyd’s story stills raises questions about this criminal who somehow won the hearts of the public.  

How does a gangster become beloved by the general public? How does such a man cement himself as such a controversial figure that 75 years later, he’s still well-known?

“Break a rule and you’ll meet friendly folks who’ve done the same.  Good folks get all the broken hearts, bad folks become a household name,” sings the character of Floyd in jazz pianist Tom Cleary’s Be Good or You’ll Be Lonely.  Debuted in March 2010 and still part of Mike Gordon’s band’s repertoire, BGAYBL caps off a cycle of songs about Pretty Boy Floyd, his wife, and his two mistresses.  While the concept-album-worthy cycle is currently unfinished, there are at least several songs already written and arranged.  Floyd was both “a ladies’ man and an occasional churchgoer,” Cleary told me, “I tried to work both of those themes into the lyrics.”  While Cleary admits that some of the story is less than historical, much of the storyline is based on facts about the often-contradictory Charles Arthur Floyd.    

The only song in Cleary’s Pretty Boy Floyd storyline thus far covered by Mike Gordon is Be Good and You’ll Be Lonely, the last track in the Floyd cycle.  A number of the other songs, some of which may enter the Mike Gordon repertoire, investigate the exploits of Floyd and his henchman.   Cleary’s Burlington, VT band Blue Gardenias will be performing a group of the Floyd songs focused on his relationships with women at Burlington, Vermont's Full Circle Festival in 2014.  In this version of the cycle, the eponymous opening song is followed by I Could Use a Fool Like You, sung by Floyd’s older mistress; I Can't Be Your Angel, sung by the younger mistress; and Come On Home, sung by his wife. All three of them then sing a trio called Love Is A Mystery. These songs are solos for three female singers in Blue Gardenias, Amber deLaurentis, Taryn Noelle, and Juliet McVicker.  

Love Is A Mystery.mp3 from Tom Cleary on Myspace.

So how does a gangster - one who killed at least 10 men - become beloved by the general public? How does a murderer and a thief endear himself to the public?

As Floyd and his gang would rob banks, they would unburden people of their debts by destroying mortgage documents (which, in a non-internet world, was the only legal proof of such arrangements, thereby relieving people of their payments).  After robbing banks, it’s claimed, he would drive up and down the surrounding streets throwing coins on the road for the townspeople to pick up.  Oklahomans protected and defended Floyd with pride, calling him the “Robin Hood of Cocksoon Hills.”  

Will we get to hear more of Cleary’s storyline of Floyd and his exploits? This author hopes so, after all “Amazing Grace don’t sound so pretty once you’ve heard those outlaw tunes.”

Watch Be Good and You'll Be Lonely on YouTube

My mama always swore
act holier than thou and
you’ll have enemies galore
but break a rule and you’ll meet friendly folks who’ve done the same.
Good folks get all the broken hearts
bad folks become a household name

Be good and you’ll be lonely,
though no one wants to know,
most Juliets smoke cigarettes and dump their Romeo
but a third rate Jesse James walks by
and every lady swoons
Amazing Grace don’t sound so pretty
once you’ve heard those outlaw tunes

So many folks will offer you free advice
and tell you that nothin’s yours till you pay full price
but you listen to them and next thing you know
you gotta borrow someone else’s dough
when your loaf of bread turns into half a slice

Even the tailor and the taxman know
that there ain’t nothin wrong
if you take something from someplace
where it didn’t quite belong.
Be good and you’ll be lonely
and that would be a waste,
if you’re walkin’ by the banquet
why not have a little taste

If you’re tryin to lie when you’re worried about what’s true
you tell lies that anybody can see through
but any decent outlaw knows
how to dress in someone else’s clothes
and make 'em look like they belong to you.

And if you go and read the gospels
you’ll see when you’re through
they’re about a man who broke the law
‘cause his daddy told him to
be good and you’ll be lonely
but I think that you’ll find
it sure can pay real good to be a little bad sometimes.

It sure pays good to be a little bad sometimes