Live at Weed’s, Chicago
Words by Kyle Smith//Illustration by Sonia Kreitzer
Those Rilo Kiley kids are off making music that allows latent fans of “Salute Your Shorts” to marry cheap nostalgic appreciation with the sheen of major label indie rock, but both Jenny Lewis and Blake Sennett’s solo projects deviate from the sly cultural references that pepper their catchy albums in favor of rustic, country-tinged Americana; both efforts are very pleasing but also hint at some disingenuous motives — their alt-country authenticity seems a purposeful stab at erasing memories of once sharing a bill with Shelley Long or Donkeylips.

If hanging out at Nickelodeon Studios and the ever-present threat of slime made these photogenic prodigies eager-to-please entertainers, then the Appalachian sets and studios that groomed fellow child actor Will Oldham can be seen as the relaxing force in Oldham’s multi-faceted career. Consider his revelatory turn as a young preacher in John Sayles’ stunning “Matewan” — his performance tempered by a spiritual fury that manifests itself in the inimitable fury of a voice that dominates every scene. Will Oldham is 15. Will Oldham is shouting. Will Oldham is angry.

It’s quite the opposite from the delicate, loving voice now synonymous with almost all of his perplexing monikers. All those variations are no mistake — from Palace to Bonnie “Prince” Billy, Oldham sees himself as more than a musician, with impeccable acting chops (“Old Joy”), impeccably understated albums, impeccable drug-taking skills (“Tripping with Caveh”), and now, it would appear, impeccable comedic timing.

Any bar worth a damn in Chicago doesn’t enforce the cities’ smoking ban, and Weeds is one such bar. They’ve been hosting a monthly stand-up show called “The People Under the Stares,” and this Tuesday night saw a show sponsored in some capacity by Drag City. Demand was so high among eager beaver Chicagoans that another show was added to accommodate thrill-seekers who were primed to be disappointed by Oldham’s presumably dubious stand-up routine. As if the guy who wrote “Raining in Darling” is going to have us buckling with each punchline. I attended only this second show, wondering while I stood in the cold exactly what algebraic equation described the following: If I like his music, why would I like his comedy?

And man, Bonnie “Prince” Billy played all of us. He took the stage — which may quite literally have been a soap box; each of the night’s performers were elevated about 4 inches — and talked awkwardly. Everyone laughed. I was reminded of a truism learned from Robert Pollard’s comedy album, The Relaxation of the Asshole — good or bad, coherent or not, onstage banter is always funny. Rock stars can get up there and squirm and speak slowly and the appreciative, polite audience will laugh along, forgetting seconds later what’s so funny.

Oldham — dressed like he just jumped off a Union Pacific freighter and rolled down the bank, with a curious hint of eyeliner — opened with small-talk and then shifted to a performance gimmick. He, Bonnie “Prince” Billy (hilariously, everyone who interacted with him referred to him as “Bonnie”), would teach us, the audience, how to heckle. This gag made his entire set indefensible: knowing his audience would likely question his comedy, he looped it back on us to encourage rudeness and interruption. And still, most people laughed reverently rather than insult our host.

His comedy was rooted in slow cadences, patient pauses, and almost-invisible details. Maybe he’s a vaudevillian Norm MacDonald? He held up posters with vulgar insults in order to teach us how to startle the performer, but each sign had writing on the back you could just barely see while Bonnie discarded it. My favorite had some lengthy insult on the front, but as he tossed it aside the words “YOU SUCK” were visible on the back.

Try as I might to remember Oldham’s quips and one-liners, comedy is a very different beast from music — a setlist is easier to recall than a handful of jokes. I do remember one heckler yelling something and Oldham firing back “That makes you my cousin.” This was the funniest thing he said, with or without context.

But Oldham’s role tonight was mostly as emcee, and he graciously introduced entertaining performances by locals Prescott Tolk and Kumail Nanjiani. Drag City head Rian Murphy delivered some found poetry that he termed “Porn-etry;” keywords and descriptors found in porn spam emails that Murphy elucidated with a cutesy, Beats-inspired diction.

Then secret headliner Zach Galifianakis took the stage and owned. The graciousness with which Bonnie passed the mic to Galifianakis (a deadpan master who incorporates a piano into his set) put the evening in perspective: Oldham, dignified entertainer, defecting to Galifianakis, clearly his better. Bonnie “Prince” Billy’s antiquated stylings make him an easy source of ridicule, but he knows that honoring old-fashioned standards with decorum and respect always translates well, no matter the stage or the subject.