Thursday, Aug. 24

The Twins Jazz Orchestra is about to take a month off from its usual Thursday night gig on U Street, making this your last chance to see him in quite a while. Well! As it turns out, your timing couldn’t be better, since this week trumpeter/bandleader Thad Wilson celebrated his birthday and will do so again on Thursday. He’ll have the orchestra at his back when he does, with what Wilson promises to be “some of the hippest music you’ve ever heard.” Take him at his word. The TJO isn’t the world’s most spit-and-polish ensemble; there’s a certain ragtag, flying-by-the-seat-of-their-pants aspect to the sound. But that just makes them hipper; they’re ready for anything and spontaneous by their very nature. And especially in their second set, the band goes avant-garde—freeform, explorative, out. The Twins Jazz Orchestra performs at 8:30 and 10:30 p.m. at (where else?) Twins Jazz, 1344 U St. NW. $10. 

Friday, Aug. 25 

One is perhaps the longest-tenured jazz resident in D.C. The other was a longtime absentee from the music, now making his comeback after retiring from his day job. Who knew they were destined to be together? Well, “destined” is a bit much, perhaps, but there’s something magical in the joining of forces between trumpeter Donvonte McCoy, who’s held down the third floor spot at Eighteenth Street Lounge for a decade now, and vocalist George V. Johnson, the District’s foremost practitioner of the art of vocalese (in which a singer sets words to famous instrumental tunes and even favorite improvised solos from recordings past). Creative singer plus groove-loving jazz quintet plus downtown party vibe (plus Belgian beer)? What’s not to like here, gang? The fun starts at 10:30 p.m. at Eighteenth Street Lounge, 18th St. NW, Third floor. Free. 

Saturday, Aug. 26

You probably know Ramsey Lewis best from his massive 1965 hit “The In Crowd” (recorded, of course, right here in Washington, D.C.). You might then be surprised to know that his career’s next major touchstone was a decade later, in funk fusion—1974’s album Sun Goddess. But it’s a straight line between those two points; Lewis in the ’60s tied himself to the nascent soul-jazz movement, and simply followed it from there to wherever it may lead. In his case, that included Arp synthesizers, Stevie Wonder covers, and a band featuring Earth, Wind and Fire founder Maurice White on drums. Lewis has wandered down many paths in his career since—his newest album, Taking Another Look, is his 80th—but his current quintet is an electric one, bringing it all back home so to speak. (And they still play “The In Crowd” every night.) The Ramsey Lewis Quintet performs at 8 p.m. at The Hamilton, 600 14th Street NW. $29.75-74.75. 

Sunday, Aug. 27 

Blues Alley has spent years, decades even, cultivating Cyrus Chestnut: giving the Baltimorean pianist a bandstand on which to evolve and mature as a performer. It’s reaped dividends, for Chestnut and the club and also for the discriminating jazz fan. During all those years he was supposed to be studying jazz, he also built up massive strategic reserves of blues and gospel resources, and he’s not shy about using them in generous and sophisticated ways. But that doesn’t mean he neglected the jazz studies at all. Indeed, any single set by Chestnut is a virtuoso recital. Any facet of music that you can dream up—rhythm, harmony, dynamics, color, the panoply of subgenres—gets subjected to the piano player’s mastery at some point in the evening. If you haven’t yet seen Chestnut play, oh, the things you’ve missed. The Cyrus Chestnut Trio performs at 8 and 10 p.m. at Blues Alley, 1073 Wisconsin Ave. NW. $35. 202-337-4141. www.bluesalley.com.