Originally published on MadeLoud, March 23, 2011

Any pop culture aficionado can tell you that the world loves a good bad guy. It’s why audiences walked away from The Dark Knight talking about The Joker instead of Batman, and why at least 90% of reality TV participants are truly repellent human beings. Things are no different in the world of music. Songwriters have a long history of lionizing anti-heroes and outlaws, but the six songs compiled below go a step further,offering redemption to some folks who are pretty much the definition of irredeemable.

The Rolling Stones – “Sympathy for the Devil”

Bad guys don’t get much badder than Satan himself. Despite its title, this classic rock staple doesn’t ask us to lend an ear to poor Satan’s plight so much as it demands that we celebrate his impressive résumé of evil. He is, after all, “a man of wealth and taste,” not just the grubby fallen angel portrayed by certain religious types. Narrated by Mick Jagger in sneering first-person, “Sympathy” finds a rather smug Devil rattling off highlights from his portfolio. These include the fall of the Russian Czars, the rise of the Third Reich and the assassinations of both Kennedy brothers. Interestingly, he usually stops short of taking direct credit for these unspeakable acts. He instead claims to have been “around” or “watching,” which would seem to point a finger at humanity for following his lead. Still, this Lucifer isn’t entirely passive. He ends his spiel with a threat that you’d better damn well give him that titular sympathy or he’ll “lay your soul to waste.”

Black Randy & The Metrosquad – “Idi Amin”

Ugandan strongman Idi Amin is perhaps the most reviled of 20th Century African dictators, which puts him atop a truly cringe-worthy list. As far as Black Randy is concerned, though, Idi is the ultimate party buddy. Thrusting his tongue deep into his cheek, the late punk-funk provocateur delivers his song as an open invitation for Amin to hit the town with him. (“You really are so freaky / With your medals and dashiki / Let’s go out to the garden / It’s time to light the tiki”) While the lyrics are obviously satirical – Randy name-checks Hitler and makes winking reference to Amin’s alleged cannibalism – the image of a regalia-clad Idi Amin strutting into CBGB with a doughy punk rock junkie at his side is fairly irresistible.

Victoria Williams – “Boogieman”

The Boogieman is one of modern mythology’s most nebulous villains, a nighttime nasty whose frightening powers are only as limited as a child’s imagination. But we’ve got the guy all wrong, says Victoria Williams on this truly strange standout from 1990’s Swing the Statue. When the soft-hearted Boogieman finds an orphaned girl while making his nightly rounds, he brings her to his home in the forest and “raise[s] her up real good.” He turns out to be a great father whose only major failing seems to be sheltering his adopted daughter too much. After he dies, the heartbroken, naïve girl falls in with a shady city-slicker who promptly impregnates and abandons her. The story ends with the sadder-but-wiser girl taking her own daughter back to the woods to raise her according to the Boogieman school of parenting. It’s the rare song that alleviates childhood nightmares even as it inspires a whole new batch of adult ones.

Randy Newman – “Rednecks”

The lines between heroes and villains were frequently blurred in the culture wars of the 1960s and ‘70s. To Northern liberals, for instance, an outspoken segregationist like Governor Lester Maddox of Georgia was an ignorant hatemonger presiding over a backwards, backwoods cesspool. But as the narrator of Randy Newman’s acerbic satire notes, that’s all a matter of perspective. Incensed by a TV talk show where Maddox gets mocked by the “smart-ass New York Jew” host and his scornful audience, the singer declares “he may be a fool, but he’s our fool.” He admits to some of the South’s racial failings, but in the same breath points out the hypocrisy of supposedly open-minded progressives who see all Southerners as “too dumb to make it in no Northern town.” As for the charge that the South is dedicated to “keeping the niggers down,” he notes that “the North has set the nigger free” – so long as that freedom is restricted to such wells of opportunity as East St. Louis, the South Side of Chicago and Boston’s Roxbury. The timeless moral, as is often the case in Newman songs, seems to be that humans are pretty horrible across the board, so it’s best not to judge.

Steve Earle – “John Walker’s Blues”

John Walker Lindh was one of the most fascinating figures to emerge the immediate aftermath of 9/11. When the California-raised 20-year-old was captured fighting alongside Taliban forces in Afghanistan in late 2001, he immediately became America’s most despised American. Steve Earle’s controversial song doesn’t excuse Walker’s traitorous actions, but it does cast them in a different perspective. Singing from Walker’s point of view, Earle speaks of an alienated, disillusioned childhood (“I’ve seen all those kids in the soda pop ads / But none of ’em looked like me”) that gives way to a fervent embrace of Islamic theology. It’s not exactly a “there but for the grace of God” tale, but it gets at a universal ennui that makes Walker seem more like a mixed-up kid than a monster. Earle knows there’s a thin line between sympathetic and pathetic.

Sufjan Stevens – “John Wayne Gacy, Jr.”

Dismissing serial killers and psychopaths as inhuman beasts is often a lazy way to avoid looking at the deeper issues behind their behavior. This disturbing track from the transcendent Illinois album is all the more effective for reminding us before John Wayne Gacy was a torture-killing pedophile, he was just another neighborhood kid. Stevens opens with eerily mundane images from Gacy’s boyhood: a drunken father, a playground injury, the neighbors who “adored him for his humor and his conversation.” After a horrifically oblique account of Gacy’s murders, Stevens muses that “In my best behavior / I am just like him.” The takeaway seems to be that even if our floorboards aren’t lined with rotting corpses, none of us is qualified to cast that proverbial first stone.