Thursday, Oct. 24

The most common—-inevitable, really—-point of comparison you’ll hear for vocalist Madeleine Peyroux is the great Billie Holiday. It’s an obvious frame of reference; Peyroux shares Lady Day’s easy, sliding phraseology and the husky edge to her instrument. Sometimes you could easily confuse one for the other. Still, don’t go looking for a modern-day Billie. Peyroux, while unquestionably a jazz singer, infuses her self-written songs with generous helpings of European cabaret and American folk and pop music. The arrangements draw from those wellsprings as well, though you’d be forgiven for hearing jazz above all else: a guitarist, she particularly enjoys using the four-to-the-bar guitar chordings of the ’30s. That touch gives her music a smoky, gauzy mystique that’s certainly got its head in the clouds of nostalgia, but is somehow firmly footed in the 21st century. Or perhaps it’s just firmly footed in Madeline Peyroux, an artist who need not be defined by a calendar. Peyroux performs at 7:30 p.m. at the Birchmere, 3701 Mount Vernon Ave. in Alexandria. $55.

Friday, Oct. 25 to Saturday, Oct. 26

When there are multi-day jazz events in D.C., Setlist usually picks out the highlights to endorse. This case is an exception. I cannot in good conscience recommend missing any of Wadada Leo Smith’s Pulitzer Prize-nominated magnum opus. The trumpeter and composer has long been one of the most ambitious and sophisticated writers in any genre of music, creating work that combines strict composition and notation with space for wide-open improvisation and interpretation, along with some composition and improvisation based on unique, stringent criteria (both within a conceptual technique Smith calls “ankhrasmation”). Even so, Ten Freedom Summers is an overwhelming piece of work. Inspired by various landmarks in American history in the ongoing struggle for freedom and equality, it comprises 19 movements for jazz quartet (Smith’s Golden Quartet) and chamber orchestra (his Pacific Coral Reef Ensemble), four and a half hours that are performed over three separate programs (Friday night, Saturday afternoon, and Saturday night). And, because Smith will perform the piece in the District, in the 50th anniversary year of the March on Washington, he will supplement Ten Freedom Summers with the world premiere of two new pieces: “The March on Washington D.C. – August 28, 1963,” and “That Sunday Morning,” a piece that reflects on the 1963 bombing of the 16th Street Baptist Church in Birmingham, Ala. Smith performs at 8 p.m. Friday, 3 p.m. and 8 p.m. Saturday at Atlas Performing Arts Center, 1333 H St. NE. $33.50 each, or $85.50 for all three performances.

Sunday, Oct. 27

There are often complaints that the jazz scene in D.C. (and those of us who chronicle it) overlooks the “traditional” (i.e., pre-bebop) jazz element therein. That is a legitimate gripe. There is a fair bit of that classic jazz style being played in D.C., and it honestly doesn’t get much play. That’s especially frustrating because there’s a regular, Metro-accessible gig in town whose only cover is the price of one beer. Mike Flaherty’s Dixieland Direct Jazz Band is not exclusively Dixieland; there’s a very strong current of Benny Goodman-style swing running through their music, and drummer-leader Flaherty plays quite a bit of even the New Orleans staples with the light hi-hat-driven approach that came in with the Count Basie band. But faulting them for not sounding absolutely, rigidly like 1923 makes no sense, being that it’s not 1923; the music is delightful. Mike Flaherty’s Dixieland Direct Jazz Band performs at 7:30 at the Zoo Bar, 3000 Connecticut Ave. NW. Free (with one-drink minimum).