Best Singing Sadsack

"Singing sadsack" is not a dis. A certain amount of sadness is a necessary trait in a good singer-songwriter. Call it duende, soul, authenticity, or emotional urgency, but without it you might as well be singing on a dance-pop record. On the other hand, you don’t want to appear morose and pitiable. So, in a way, being the second saddest songwriter is a pretty enviable position. It means you possess the gravity to move your audience, but you’re not driving your fans to dress up like Brandon Lee in The Crow. Let’s examine some of the city’s finest moderately depressing singer/songwriters and name their saddest song.

Best: John Bustine, “Where Has Your Husband Gone, Donna?”

Death. Debt. Desperation. Frankly, there’s not a lot of sunshine on this spare and somber acoustic ballad about a woman who has to figure out how to feed her kids after her husband goes and drinks himself to death. Donna, Bustine’s heroine, does what any loving mom would do given the circumstances: She turns on the red light, walks the street for money, not caring if it’s wrong or, you know, if it’s right. That’s one way to keep your kid in Capri Suns. Pretty heavy stuff, for sure. Bustine just won’t settle for second place—on this song he’s making a run for the finish line with his eye on that tear-filled loving cup.

Second: Justin Jones, “Charlotte”

Justin Jones always sounds kind of happy-go-lucky, even when he’s singing about getting kicked to the curb by his ladyfriend. During the verses, he quietly wallows and ponders the details of his estrangement. Where did things go wrong? Where did all that magic go? And the chorus, “I’m going insane,” isn’t quite the uplifting turnaround you might have been looking for. But the rest of the band eventually drops in with a tidal wave of alt-country sounds (lap steel, electric guitars), and throws enough cheer on the proceedings to keep Jones from getting funereal, placing him in the perfect position to scoop up second place.

Third: Sean McArdle, “56th St.”

Steeped in yearning and romantic nostalgia, “56th St.” has the ammunition to be a major heartbreaker, but McArdle (a former Washington City Paper staffer) defuses the drama with a few doses of self-effacing humor. “We walked out under a winter moon/My friends snort Ritalin in your bedroom,” he sings, fondly recalling those smellier, punkier days when one man’s ADD medication could be easily turned into an evening’s entertainment.The instrumentation—layers of twinkling finger-style guitars and soft piano melodies—also prevents the song from strolling into downer-ville. It’s eloquent and wistful but low on out-and-out suffering.

Honorable Mention: Laura Burhenn (basically any song she has written)

Former Georgie James member Laura Burhenn certainly has an expressive set of pipes—they’re able to wander up and down the octave register with astonishing grace. So logically, of the parties examined here, she should be the most capable of really locking in to that perfect level of ennui. But no, most of her older songs, like “Helicopters” or her cover of Leonard Cohen’s “Chelsea Hotel No. 2,” sound too damn drowsy to get you down—it’s sort of like listening to Sarah McLachlan sit down at the piano after an Ambien and three cups of chamomile tea. Add in her peppy Georgie James songs and Burhenn isn’t the second saddest, or even the 10th saddest. Get a little heartbreak into this woman’s life!