Nina Nastasia and Bonnie "Prince" Billy at this year's Letters to Santa benefit

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Nina Nastasia
  • Nina Nastasia
This year is the tenth anniversary of The Second City That Never Sleeps: Letters to Santa, the 24-hour holiday benefit organized by Heather Whinna that raises money to provide relief to needy families in the Chicago area. As usual the event takes place at Second City, beginning at 7 PM on Tuesday and concluding the following day at the same time. Comedians involved include TJ Jagadowski, Tim Baltz, and Brendan Jennings, but what attracts me is always the music lineup, and this year is no exception: the Mountain Goats, Jeff Parker, Danielson, Nora O'Connor, Robbie Fulks, Helen Money, the Blisters, and more. That "more" includes two artists making their first Chicago appearances since releasing new albums—Nina Nastasia and Bonnie "Prince" Billy.

Nastasia released her latest album, the gorgeous Outlaster (Fat Cat)—her first since 2007's You Follow Me—in summer 2010. She made it in Chicago with Steve Albini (Whinna's husband) at Electrical Audio, augmenting her beautifully stark folk-rock songs with carefully measured string arrangements. Nastasia sings directly, without ornamentation or affectation, elegantly shaping her subtle melodies and imbuing them with just the right touch of vulnerability. Because I do so much of my record reviewing while writing show previews, sometimes I overlook new releases by artists who don't play in Chicago to promote them—and Nastasia's album falls into that category. This is a real shame—it's one of the best records I've heard from 2010, even though I only listened to it once in 2010. Below you can check out a song for yourself.

Bonnie Prince Billy
  • Bonnie "Prince" Billy
Will Oldham has been releasing excellent recordings all year, but he most recently performed in Chicago in May at Pritzker Pavilion, where he previewed material from Bonnie "Prince" Billy's excellent Wolfroy Goes to Town (Drag City), the first effort with his current working band—which includes Chicagoans Emmett Kelly on guitar, Ben Boye on keyboards, and Angel Olsen on vocals. He's participated in Letters to Santa before, and earlier this year he released two ten-inch singles with various collaborators to benefit three different charities, including the gulf coast cleanup and a water purifying campaign in Haiti.

Not only is Oldham maintaining a pretty good track record when it comes to good deeds, he's operating at a mind-boggling peak as an artist. Though over the past decade or so he's more or less settled on a folk-rock sound, by working with a revolving cast of musicians he makes albums that always feel different from one another. He's a brilliant songwriter and singer, and he's also smart when it comes to finding collaborators. On "New Whaling," the delicate harmony singing by Olsen and Kelly gives the tune an ethereal richness, with Olsen summoning the sound of classic British folk in all of its mannered glory. I think there's a tendency to take Oldham's work for granted because he seems incapable of making a dud, but that's not really fair. It seems like every new album ends up as one of my year-end favorites, and this one is no exception. Below you can watch the video for a track from the new album, "Quail and Dumplings," which features an acting role by Nastasia—she lip-syncs Olsen's vocal.

You can buy tickets to Letters to Santa at the door tomorrow evening for $20. If you can't make it, live out of town, or only want to catch certain parts of the extravaganza, you can watch live with a suggested $10 PayPal donation. Nastasia will play tomorrow night at 9:30, and Bonnie "Prince" Billy will take the stage at 5 AM on Wednesday morning (what a trooper).

Nina Nastasia, "You Can Take Your Time"

Bonnie "Prince" Billy photo: Dirk Knibbe

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