Wilder Deitz, a Planned Parenthood benefit, and more events of note in Madison this week.

Sponsor message: The weekly Tone Madison calendar is made possible with support from Union Cab of Madison, a worker-owned cooperative providing safe and professional taxi services.

THURSDAY DECEMBER 20

Kurt Vile, Jessica Pratt. Sylvee, 8 p.m.

Kurt Vile’s seventh solo record, this year’s Bottle It In, continues to clean up the gloriously messy blueprints he laid out on earlier albums like 2008’s Constant Hitmaker and 2009’s Childish Prodigy. But the Philadelphia-based singer-songwriter maintains his psychedelic edge here by allowing his heady lyrics to unravel organically over droning folk-rock backdrops.

Even on more focused, single-friendly folk-rock cuts like “Loading Zones” and “One Trick Ponies,” Vile’s understated, atmospheric, and Tom Petty-channeling pop feel is countered with his specific brand of contemplative isolation. When Vile croons, “Looked down into a deep, dark well / Called all your names / They echoed down for miles and miles / And all that other mystical, well, never-you-mind” on “One Trick Ponies,” it’s as though he’s giving the listener a seat inside his brain. While Vile’s warm, distinguished guitar tone and comforting croons help him standout amongst thousands of would-be troubadours, his real strength is in taking the sound of a lonely hitchhiker singing to himself as he walks down an empty highway and making it palatable.

Los Angeles-based folkie Jessica Pratt opens with her stripped-down blend of breezy vocals and jazzy chord progressions. Pratt is currently touring ahead of her forthcoming album Quiet Signs, a collection of stoney morning folk tunes. —Joel Shanahan

FRIDAY DECEMBER 21

Ben Ferris Octet. North Street Cabaret, 8 p.m.

Madison jazz bassist and composer Ben Ferris has a holiday tradition of sorts that plays off the mixture of affection and annoyance most of us feel toward Christmas music. At this annual holiday show, Ferris and his octet will be prepared to play both Christmas songs and an assortment of non-yuletide-themed originals and standards. Audience members can nudge the band toward or away from Christmas music by dropping tips into one of two tip boxes, labeled “ho ho ho” and the other labeled “no no no,” or by verbal vote. Inevitably, there will be at least some seasonal material, which Ferris says will include selections from Wynton Marsalis’ 1989 album Crescent City Christmas Card and Duke Ellington’s arrangement of The Nutcracker Suite. Clarinetist Karl Busch and vocalist Rose Heckenkamp-Busch will be at this show to augment the octet’s core lineup of saxophonists Nicholas Bartell, Jon Hoel, and Luke Busch; trumpeter Paul Dietrich; trombone player Darren Sterud; pianist Paul Meunch; and drummer Michael Koszewski. To hear more of Ferris’ originals, give his 2016 album Home a listen. —Scott Gordon

SATURDAY DECEMBER 22

Wilder Deitz, Alex Franzen, The Earthlings. Communication, 7:30 p.m.

Madison-based pianist and composer Wilder Deitz, along with a stellar rotating cast of collaborators, has been doing some compelling work in recent years around a nexus of funk, jazz, and hip-hop. One show this fall at Art In found Deitz playing a Fender Rhodes and providing bass lines with a Microbrute synthesizer in a quintet. The band slayed a crowd mostly composed of people who’d never seen the group before. One high point was the band’s grindingly funky, unapologetically raunchy cover of Ginuwine’s “Pony,” led by vocalists Deja Mason and Bobbie Briggs, but Deitz and company more often push deeper into thematic and harmonic territory. On 2017’s limited-edition Summer Mixtape, an eight-piece incarnation of the Wilder Deitz Group brought together elements of spoken word, breakbeat hip-hop production, New Orleans jazz, and other disparate strands, collaborating with a few local MCs along the way.

Operating in a similar spirit here is Madison-via-Minneapolis saxophonist/composer Alex Franzen, playing here to celebrate the release of his first solo album, All Of Me To You. Franzen pulls together threads of jazz, classical music, and bright, synth-streaked R&B, with Madison-based MCs including Dudu Stinks and Protege The Pro turning in solid features. In a somewhat gutsy twist, the record also served as Franzen’s marriage proposal to his then girlfriend and now fiance. Madison electronic-rock outfit The Earthlings rounds out this bill. —Scott Gordon

Creatures Stirring: Benefit for Planned Parenthood. Art In, 6 p.m.

This seven-band fundraiser show for Planned Parenthood boasts a killer variety of local music, with arts and crafts for sale for the cause as well. Madison’s music community needs more genre-colliding events like this. The highlights range from Olyvia Jaxyn, who used their aching baritone to create ethereal but accessible pop on the 2017 EP Lyv, to Ruin Dweller, a full-on filthy death-metal band featuring members of Dosmalés and Jex Thoth. The latter’s debut EP, Cryptic Ruin, made Tone Madison‘s top 20 Madison records of 2018 list. Clean Room, Darker N’ Darker, and Bashford give the bill a heavy emphasis on fun, grimy rock ‘n’ roll, but there are further curveballs in store, thanks to the eccentric electronic pop of Tippy and the wide-ranging psychedelic folk of Gods In The Chrysalis. If you’re still in town for one pre-Christmastime show, make it this one. —Scott Gordon

ALSO NOTED

12/20: John Statz Trio, Robby Schiller. North Street Cabaret, 8 p.m.

12/22: A New Orleans Christmas with Leroy Jones. Café Coda, 8 p.m. (sold out)