Legendary Songwriters Who Have Never Shied Away From Inhabiting Unsavory Characters

Certain songwriters show no fear when it comes to portraying characters who might not be all that honorable. It’s a brave move to make. If you do it, these artists run the risk of people thinking that they are that character and not simply a writer using their imagination.

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We’ve listed two individuals and one songwriting team below who have proven themselves in this particular skill time and time again. They’ve enlightened us by going dark.

Randy Newman

People who only know Randy Newman as the jovial voice behind animated movies like Toy Story might be surprised to find him on this list. But in his guise as a singer-songwriter, Newman has inhabited characters who are racist, misanthropic, and filled with every imaginable vice. That willingness to delve into the hearts and minds of these people immediately set him apart in the genteel, soft-rocking days of the early 70s.

Newman dared to write from the perspective of a slave trader in the song “Sail Away”. On his album Good Old Boys, he delivered “Marie”, which comes on like a romantic ballad but actually offers a laundry list of the narrator’s weaknesses. And Newman took aim at silly prejudices on “Short People” by pretending to be someone who thinks the titular group of folks should be persecuted. All these bold moves paid off thanks to Newman’s biting wit and piercing insights.

Warren Zevon

Warren Zevon always gave the impression that his own personality wasn’t all that far removed from what the ne’er-do-wells within his songs had to offer. His unapologetic embrace of protagonists who lived on the edge and left a wide trail of damage behind them helped him separate from the songwriting pack. Even on his last album, as he was on the cusp of death, he sang nostalgically about his “Dirty Life And Times”.

“Lawyers, Guns And Money” set an early high bar in terms of Zevon narrators whose self-destructive tendencies were on full display. Not for nothing did he title a song “Mr. Bad Example”. It was Zevon’s great skill that he somehow made these folks sympathetic, even lovable. His own performing charisma had a lot to do with it, as did the eloquence and humor of his words.

Mick Jagger and Keith Richards

Mick Jagger and Keith Richards must have inherently sensed that they needed to set themselves apart from The Beatles. While the Fab Four projected a pristine image, the Glimmer Twins willingly embraced the seamier sides of life in their songs right from the start. That dovetailed with the outlaw façade that they constructed for The Rolling Stones, especially early on in their career. When these guys tried to lighten up and go the flower-power route, they faltered.

Jagger made a habit of including at least one set of lyrics per album that shredded any notion of political correctness. Meanwhile, Richards often wrote songs like “Before They Make Me Run” that winked knowingly at his own legal struggles. Throughout the years, Jagger and Richards have often squabbled. But when they put up a unified front of reckless debauchery, they’re pretty difficult to resist.

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