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  • Writer's pictureKurt Keefner

Fun Songs about Bad Men

Updated: Nov 24, 2022

[Editor's note: Today's installment of "Sifting the Sands" consists of my friend Fundal interviewing my friend Serio. Both are renowned writers about art and music, sometimes referred to as the Siskel and Ebert of culture criticism. Serio's latest book Interrogating the Music: A Thoughtful Approach to Popular Song has just been published by Penguin, Random House, & Schuster, while Fundal's newest, Letting It Be: Learning to Enjoy Music Without Judgementalism, is due out next month from HachetteCollins. The transcript has been lightly edited for clarity, length, and good manners.]

FUNDAL: It's good to see you again, Serio.

SERIO: Likewise, Fundal.

FUNDAL: Shall we say a bit about our new books?

SERIO: Let's consider them plugged. I want to get down to it.

FUNDAL: Right. So I gather you've got a new burr under your saddle. Care to tell me about it?

SERIO: Of course. What's bothering me this time is how wicked men are celebrated in popular music.

Photo by Abbat on Unsplash

FUNDAL: Well, insofar as celebrations are usually fun, I might like such songs where you don't, although I suppose even I would draw the line somewhere. But I'm guessing that I'm a lot more permissive than you are. Care to share an example?

SERIO: Yes. Here's one:

FUNDAL: Wow! Haven't heard that one for awhile! It's really cool.

SERIO: Yes, I would say that Darin is trying to out-Sinatra Sinatra.

FUNDAL: Well, he's never going to unseat the Chairman of the Board, but I really like this. What exactly is wrong with it in your opinion?

SERIO: Darin is trying to be hip about a man who stabs women to death. A lot of women. So many women that they have to stand in line to be murdered. He delivers bit of scatting, a twirl, and some terms of endearment to the listener. And then the big finish: "Look out, Old Macky's back!" Makes him sound like the cool guy of the neighborhood returning after a stint in the army.

FUNDAL: I think you might be taking it a bit too seriously.

SERIO That's my nature. I have a vivid imagination and I see the things the words are saying as if they were real.

FUNDAL: I'd like to think I have a good imagination too! Would you rule out all music with violence?

SERIO: No, it depends on how it's presented. For example, I have no objection to the old "murder ballads," even though some of them are quite gory. They can be quite exciting without celebrating the murderer. "Pretty Polly," which has many versions, is a traditional murder ballad. This 2013 reimagining of the song by Vandaveer is quite atmospheric and chugs along quite nicely.

The songs I object to, which are generally modern, make bad men sound cool, which almost none of the murder ballads do. Mack really is evil, which is obvious even in Bobby Darin's version of. But we're distracted from Mack's violence by Darin's Las Vegas stylings.

And it's not just the swing and pizzazz of the music that celebrates Mack; it's the words. Darin sings "babe" and "dear" to the audience and says "Could it be our boy's done something rash?" and "lies a body just oozing life." The words and the music work organically to make Mack and his murders seem hip.

The song didn't start out this way: "Mack the Knife" is an update of a song on the same subject that doesn't glorify Macheath.

FUNDAL: You are referring of course to "Die Moritat von Mackie Messer" from Brecht and Weil's The Threepenny Opera, a German play with music from 1928.

SERIO: Yes. A "moritat" is a medieval murder ballad played by strolling minstrels. The Threepenny Opera tells the story of Macheath, a criminal who marries the daughter of the boss of the beggars. The father disapproves and gets Macheath condemned to the gallows, but Mackie is reprieved at the last moment by Queen Victoria, who makes him a baronet, thus allowing him to legally be a criminal. Lyricist Bertolt Brecht, who was a socialist, intended this as a condemnation of capitalism, although that's a real stretch.

FUNDAL: Yes. And as you say, "Mackie" is far worse than "Mack."

SERIO: Right. Mackie burns down a house with seven children in it and rapes a young widow. This is Lotte Lenya's 1955 recording. It's in German of course, but listen to the first couple of verses to get the style. There's no "babe" or "dear" or women standing in line or anything like that. That's was all "found in translation."

FUNDAL: I like it. It's droll and ironic. Mackie does these crimes and no one can prove it, just like capitalists get away with everything. But Bobby Darin's swinging version is a lot more fun, you would have to agree.

SERIO: Yes and no. They're after different things. The German version is more horrific but it doesn't celebrate Mackie's immorality. The Bobby Darin version swings, but it feels "off" to me and makes me uncomfortable. It's creepy, even though it sanitizes its subject by omitting the arson and rape.

"Mack the Knife" has been translated into many languages (including Icelandic!) and performed by many, many artists. Most are doing the hip, Bobby Darin arrangement, but there are other styles. Here's a slinky, seductive, and decadent cabaret-style rendition by Ute Lemper. If you're looking for an English-language version that provides the flavor of the original check out "The Ballad of Mack the Knife," sung by Robyn Archer. John Willett and Ralph Manheim did a clever adaptation of the German lyrics that stays true to the spirit of the original.

FUNDAL: Well, I sort of see what you're saying about the swinging versions of "Mack the Knife," but to me they really aren't any more disturbing than fiction about bad guys in general. Maybe another example would help.

SERIO: Okay. The appeal of "Mack the Knife" is that it swings and can be made to sound hip. But there is another song, or rather, group of songs that can be used to make the same point more vividly. You are of course familiar with "Stagger Lee"?

FUNDAL: Yes, it is the primordial "bad man" song. It's based on a real person, a pimp named Lee "Stack" Shelton who murdered a friend of his, Billy Lyons, in 1895. The two men had gotten into a scuffle over politics in a bar. Lyons snatched Shelton's Stetson hat. Shelton shot him in the belly, took the hat and walked away. He was convicted of the murder and sentenced to 25 years, but only served 12. He died in prison after being convicted of another crime.

SERIO: There are many versions of Stack-o-Lee, Stagolee, and Stagger Lee out there. It appears to be a true folk song, originating among Black people in the cotton fields and spreading with different verses and different tunes for years before anybody wrote any of it down or recorded it. I would say that there are two paradigmatic versions. The first is by Mississippi John Hurt from 1928.

FUNDAL: That's some classic country blues! The bad guy sure isn't celebrated here, and it's a lot of fun to listen to. However, I know what what you're going to compare Hurt's version to.

SERIO: I'll bet you do. And I'll really make my point with this hit from 1959.

FUNDAL: Okay, I have to give you this one. While it's decent R&B or maybe early rock 'n' roll, the background vocalists chant "Go Stagger Lee, Go Stagger Lee," like they're cheering him on. His wickedness is a party. And it ends without Lee being punished or even arrested. Completely amoral.

SERIO: So you agree that I'm picking up on a real problem? Have I won you over to my point of view?

FUNDAL: Well, not completely. But I'm more willing to keep an open mind. Stagger Lee, in its Price arrangement, has been covered many times, yes?

SERIO: Yes, cringe-inducing covers like Pat Boone's. There are a couple of good variants that do not use the Price arrangement. Taj Mahal did a live update in 1993 of Mississippi John Hurt's version with a wonderful, ringing acoustic guitar. Another worthwhile version is blues-rock duo The Black Keys's intense, stripped down fuzzy-electric version from 2004, titled "Stack Shot Billy." The Keys distill it down to its essential portrayal of Stack's evil and eternal punishment. There isn't even a Stetson hat! You can tell something has become an archetype or a meme or myth or whatever when it gets reworked in that way. However, in the age of recordings and radio, it is possible for one version to become "definitive" and influence almost everything that comes after. That makes variants even more special because they are independent. [You can read more about Stagger Lee here. -ed.]

Anther variation on the bad dude song, less appealing to me, would be Jim Croce's 1973 hit "Bad, Bad Leroy Brown." Notice that in this song the narrator uses Black Vernacular English ("Baddest part of town," "He stand about six-foot four," "He got a .32 gun in his pocket for fun," "the two men took to fighting," etc.) And the ladies call Leroy "treetop lover." That says "jungle man" to me.

Most of Croce's work is quite sensitive, but for "Bad, Bad Leroy Brown" he applies a thick layer of blackface. Black is bad dude. Black is outlaw. Black is free from all of those tight-ass inhibitions White people have. Black is cool. That's the same image of the Bad Black Man that gangsta rap has employed since then, only now some Black men are doing it to themselves. Minstrelsy isn't dead; it just changed its form. It's still as degrading as ever.

FUNDAL: Well, that's harsh.

SERIO: Not if it's deserved. Look, it's not that I object to songs about bad Black men. Lee Shelton was Black, and I think that we're supposed to assume that Stagger Lee is too, partly because the two paradigmatic versions of the song were sung by Black men in what would be regarded in their day as Black styles. And it's not that only Black people can sing about Black people. The Black Keys are White and they use a style (electric blues) that derives from Black music. But they're not practicing "cultural appropriation" in any vicious sense. In any case, none of these musicians are mugging for the listeners like Jim Croce, not even party-man Lloyd Price.

FUNDAL: Although I am somewhat sympathetic, I think some of our listeners would pooh-pooh your analysis of "Leroy Brown." First of all, it's fun. Furthermore, perhaps we are meant to think that we are less celebrating Leroy's world and more that we are experiencing how it sees itself. The music and words are the soundtrack of Leroy's story, not ours. After all, Leroy does get cut up in the end, which demonstrates the ultimate failing of Leroy's approach to life. It's a moralistic tale.

SERIO: That's intriguing, and I'll have to give it some more thought, but provisionally I would say that if that is the case, then the song is trying to have it both ways. It's mostly celebratory but puts a little moralism at the end to keep it from being a story of thorough depravity, but we are clearly supposed to enjoy seeing the badness of Leroy throughout the song.

FUNDAL: At least one artist I can think of doesn't share your view of the necessity of morality in song, and that's Billy Preston, who in 1972 sang "I've got a story, ain't got no moral / Let the bad guy win every once in a while."

By the way, the development of archetypes and memes in music would be a great topic for discussion another time! In fact, our esteemed editor has written about it here. But now maybe we should check out some other examples of the celebration of bad men. How about Bonnie and Clyde, the notorious 1930s bank-robbing couple? There were several songs about them.

SERIO: Songs, books, and movies, as well as stage musicals and a Looney Tunes cartoon. The Barrow Gang murdered 11 people and were hideously injured themselves during their pursuit. But because Bonnie Parker wrote some doggerel and a few "cute" photos of themselves posing with guns were published in the newspapers, they became a media sensation during their crime spree, at least until they killed two police officers too many.

FUNDAL: Definitely a cultural phenomenon. The high point, if that's what we're going to call it, would have been the 1967 film version starring Warren Beatty and Faye Dunaway, which pushed the limits of violence in a Hollywood movie. It was not a complete glamorization. Clyde is portrayed as impotent and his brother and sister-in-law were casualties of crime before Bonnie and Clyde's gruesome end, but the overall tone was fun. It uses Flatt and Scruggs's zippy 1949 bluegrass instrumental "Foggy Mountain Breakdown" for a chase scene.

SERIO: I'm not sure whether Flatt and Scruggs approved the use of their song in the movie. Ironically, they did a 1968 story song account of the spree titled "The Story of Bonnie and Clyde" which narrated the events without passing judgment. It's basically a bluegrass murder ballad. However, the song I wanted to point out was Georgie Fame's "The Ballad of Bonnie and Clyde," which reached #7 on the Billboard Hot 100 List and was inspired by the film of that year.

The words aren't so bad, but the music is a corny mix of ragtime, jazz, and rhythm and blues, all punctuated by he sounds of gunfire and sirens. It's like something like Randy Newman, the guy who did "Short People," would do. Murder is quirky good fun apparently. Interestingly, there is no definitive Bonnie and Clyde song, unlike what we saw with "Mack the Knife" and "Stagger Lee."

The coolest version, however, is in French. Sung by Serge Gainsbourg and Brigitte Bardot, the words come from Bonnie Parker's actual poetry about the Barrow gang, with some wild whoops as accompaniment.

FUNDAL: That's surreal, but it's clearly somebody's idea of romanticism. It certainly does get coolness points, though: five for Gainsbourg, five for Bardot, and five just for being in French.

I admit you've got me thinking. Beyond a certain point (and you and I probably disagree on where that point is) there's something not quite right about songs that could be described as a celebration of wicked people. Following up on Bonnie and Clyde I would mention Steve Miller's 1976 hit "Take the Money and Run." It's another song about a couple on the lam. They shoot a man "while robbing his castle." They never get caught. Ah, to be young and fun and carefree!

SERIO: Fortunately, there is an antidote to "Take the Money and Run" and "The Ballad of Bonnie and Clyde," and that's Bruce Springsteen's 1982 minimalist song "Nebraska," from the album of the same name. It's a first-person account, delivered from the electric chair, of Charles Starkweather, a real 19-year-old who with his 14-year-old girlfriend killed ten people in 1958. It's not celebratory. In fact, it's something of a dirge, but it is certainly authentic.

FUNDAL: I sense a conflict between authenticity and fun for you.

SERIO: Not true. I like fun music, even fun music about bad people, although that might be too light-hearted a term for the kind of pleasure I derived from a good song about a bad man. I just don't like music that clicks its heels about bad people.

FUNDAL: OK. So now we have three sets of examples—Mack the Knife—Stagger Lee—Bonnie and Clyde. Do you have any one-offs you'd like to mention?

SERIO: How about Michael Jackson's "Smooth Criminal"? The song itself is horrifying. A man breaks into a woman's apartment. He sheds her blood onto the carpet. She hides under a table and tries to escape into the bedroom. He follows her and attacks her, but she doesn't die right away. Rescuers try mouth-to-mouth resuscitation, but she dies anyway. It is the only song in our sample where we feel the victim's terror. But the video of the song, which contains some impressive dancing, has a completely different plot. In it, fedora-wearing Michael Jackson makes a cool entrance into a night club where he proceeds to destroy a number of thuggish looking gangsters. I don't think Jackson had the guts to make the video match the nightmare that was the song.

FUNDAL: Yes, the song is gruesome, and yet I had to laugh at the idea of Michael Jackson being a tough guy. It was almost as hilarious as when he sang "I'm Bad."

SERIO: I've always thought he was over-compensating, but who knows what went on in that mind of his.

FUNDAL: OK, we could go on all day piling up examples. But I want to know how you separate the good songs about bad men from the bad songs about bad men. What is your thought process? Is it a process other people might want to try for themselves? People are very attached to their musical tastes. It seems like it's a hopelessly subjective area of life. Could your way of listening to songs ever change anybody's mind?

SERIO: What I do first of all is listen closely and literally to the words. They might be celebratory in themselves. Mack kills many women—he even names them—and it's treated in a dashing manner. Lloyd Price's Stagger Lee is cheered on by the chorus. Words are important; they're not just an excuse for the music.

And I listen to the music too. Primarily, I try to identify it by genre. Not the formal and broad genres like jazz or rock, but more specific stylings. "Mack the Knife" is Rat Pack style (which I think tends to be overly cool and a bit phony). Even without combining the music with the words, I can sometimes tell how authentic a song it. "Take the Money and Run" is obviously silly 70s pop-rock—musical Cheetos to satisfy the aesthetic munchies. I suppose if it were paired with something equally frivolous it might be harmless music to smoke weed by, but it isn't.

The next step is to put the music and the words together and look for incongruities and reinforcements. The hip music and cool words of "Mack the Knife" reinforce each other. I don't get that from "Mackie Messer" because the music isn't trying to be hip and the words aren't either. The song is droll and cynical, and that is appropriate for a criminal who gets away with murder in a society that does not punish thieves and murderers. Darin's version is quite disturbing.

FUNDAL: Disturbing? Why should it bother you? Mack doesn't exist and neither do the women!

SERIO: Neither do the people who get tortured in horror movies. But many viewers are disgusted and terrified by the portrayal of such events.

FUNDAL: Yes, but many other people regard them as thrilling or even funny.

SERIO: I suggest that many such people have a problem.

FUNDAL: I have to go along with you there. Many or most horror movies, especially since Night of the Living Dead, have been gross, and people who revel in them are inappropriately treating them as mere entertainment. I still think my larger point stands, though.

SERIO: Well, I think that in a way we have to treat the characters and events in art as real for the art to work on us, even though we know they aren't. We bracket them. In the case of celebrating bad men, I think we're having it both ways: we treat badness of the characters as just real enough for us to have fun with them but not to real as to make us feel guilty for reveling in them.

FUNDAL: Ah guilt! You're in danger of trying to impose a moral standard and guilt trip people over their tastes.

SERIO: I don't mean it that way. What I am saying is that if you choose to be sensitive and thoughtful about art (and, for that matter, about life) you will be naturally drawn to what is healthy and repulsed by what is not. You're not forcing yourself to be "moral" because you feel guilty. Rather, you are taking things seriously, listening to your inner voice and feelings, and so forth. That's not an imposition; it's openness to experience at the highest level.

One thing I find troubling in many music-lovers is that they discover something to love when they're 17 years old, and they never move beyond it. It becomes part of who they are. That's why people resist the kinds of criticisms I make. At best they think they are absurd because they go against the certainty of their bedrock identity, which they take as much for granted as the air. At worst they take them as a personal attack and become defensive.

FUNDAL: Well, it takes a lot to make me defensive. I'm too self-sufficient. Besides I know that you don't mean what you say in a hostile way. But as far as challenging another person's identity as realized in their musical tastes goes, that seems futile at best.

It seems to me that we approach music, and I suspect, life in different ways. I think art and life should just come at you and swallow you up. That's the best kind of experience for me. What you're saying reminds of that line from Wordsworth: "We murder to dissect." Your relentless analysis kills the joy of the immediate experience. People just don't want to let that happen to the things they love.

SERIO: I admit that sometimes I am a bit rationalistic. I regard that as an occupational hazard for my way of life. But I think my approach is still quite joyous. When it comes to music, I listen to a song three times: first, for the immediate experience; second, critically; third, for the experience again, but this time informed by insight. I don't have to literally listen three times of course; I can collapse the listenings into two or maybe even one.

That third listening is usually the best for me. By listening critically, I have resolved what seems "off" about the song so I can integrate all of my impressions and appreciate the song for what it is including its deficiencies, which I can now—usually—regard as mere blemishes. This might still involve more distance from the music than you would like. Actually, I do as an adult enjoy Bobby Darin's "Mack the Knife"—just with some cringe at the lyrics and an ironic attitude toward Darin's hip cavorting. However, I draw the line at Lloyd Price's "Stagger Lee" festivities. If I want a dose of bad Stack, I'll go to The Black Keys.

Ultimately, however, I think enjoy the songs I do like just as much as you enjoy the songs you like. And I would argue that my experience is perhaps richer and and possibly more satisfying to me because I listen with all my faculties and not just my passions.

FUNDAL: Whoa! You're making a lot of assumptions about me, buster!

SERIO: I apologize for any presumptuousness. But am I really being unfair?

FUNDAL: From your perspective, maybe not. But I still bristle when someone acts like they've got my number and condescends to me.

SERIO: I apologize again. You know how much I respect you, your enthusiasm, and your decency.

FUNDAL: You just don't believe I think enough.

SERIO: In a way, I don't believe anybody thinks enough. Or listens to their feelings enough. As a critic what I hope is for people to examine more explicitly what's there in the music and to be sensitive to their own reactions. In addition, people should ask themselves why they like what they like instead of taking their tastes for granted.

FUNDAL: Well, this brings us to the $64 question: Why do you think people like songs that celebrate bad men?

SERIO: I think it's several things, most of them uncontroversial. First, to be successfully bad, even in the short run, means to be strong, daring, and uncaring about public opinion. That's exciting. Second, badness subverts both our boring, conformist middle-class lives and the social mores that we may feel hold us down. Badness says "I do what I want, not what my parents, the boss-man, or the government tells me to do." That kind of Wild One rebelliousness is attractive, at least to people who don't much suffer the consequences of it.

And there's an element of resentment too, perhaps occasionally justified. The banks that some robbers rob sometimes cruelly foreclosed on poor people and took their homes. Legend has it that 1930s gangster Pretty Boy Floyd would burn mortgage records, and in Woodie Guthrie's telling of his story he even feeds folks who are on relief.

Many women like "bad boys" and many men wish they could be bad boys. Songs that celebrate bad people are parties for the devilish side of some people. Goody-two-shoes is boring and unmanly.

There is an underlying historical dynamic at work here. The two-thousand-year Christian emphasis on meekness creates a false dichotomy between virtue/weakness and vice/strength. Add to this the general Christian/professional emphasis on restraint and modesty and the dice are completely loaded. Many people find virtue confining or boring, In addition, there is the widespread notion that the hero is the one who is the one who is at the top of the heap, which means he dominates others, which means he might use some form of coercion, be it intimidation or outright violence. Put it all together and you get that people like to celebrate bad men because they are alpha males. People do insane things under the influence of charisma.

You can see how what might seem unimportant to some people—popular music—is actually critically important: how we listen to music reflects how we look at life. Today's conversation's focus on fun music about bad men is really just an excuse for this larger point.

FUNDAL: Oh, Serio! Always looking out for his fellow man! I will say that the next time I hear a song about a bad man, I will not just take the fun experience for granted. And maybe I will take a more deliberative attitude toward music in general. At least when that doesn't completely spoil the fun!


FUNDAL: Can we go out on a song about a bad man? I think you might like it.

SERIO: Oh, wow! This 2003 gem features The Man in Black singing about a man who surely wears black! I love the way the nursery-rhyme vocal melody plays off the crunchy electric-blues guitar! It's a little playful as it shows the villain falling into evil while tossing off drolleries, but the guitar keeps it serious. Boy should've listened to his mama! Fun in the best sense!

FUNDAL: Well, Serio, thank you for a good discussion. You've given me a lot to think about.

SERIO: Then my work here is done! Thank you!


If you enjoyed this piece you might also enjoy this collection of essays: Killing Cool: Fantasy vs. Reality in American Life.


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