TUESDAY, DECEMBER 18
The debate over the best version of “Both Sides Now” may rage on for eternity, but Judy Collins certainly gets points for scoring a Grammy in 1968 for her version of Joni Mitchell’s epic, life-summarizing song. Problem is, Mitchell also won a Grammy in 1969 for her album Clouds, which features her recording of the tune. Alas, you’ll have to decide on your own (if you haven’t already), starting with a visit to The Birchmere, where Collins will perform Tuesday and Wednesday. Show 7:30 p.m. $59.50. All ages, accessible venue.
The Twitter bio of D.C. singer-songwriter Felix Pilar reads “I hate bands & music almost as much as I hate my own bands & music.” And his music is equally honest, with songs such as “Narcissism,” delving into inner turmoil over confronting one’s sexuality. Hear him at RhizomeDC. Show 8 p.m. $10. All ages, inaccessible venue.
WEDNESDAY, DECEMBER 19
If you need a day brightener, play Armani White’s latest single, the revelatory “Onederful,” on repeat. The young Philadelphia rapper, who took a two-year hiatus from the music industry after losing his father to cancer, is back and is one to watch. Catch him at Songbyrd. Show 8 p.m. $15-$18. All ages, inaccessible venue.
THURSDAY, DECEMBER 20
The titles of most Cupcakke songs are definitely NSFW, but her hard-hitting rap style and lyrics are something to savor (including name-dropping Stacey Dash at 1:57 into “Dangled,” which is apparently on trend this year). Catch her at The Fillmore. Show 8 p.m. $12.50-25. All ages, accessible venue.
North Carolina band Hiss Golden Messenger may be branded “folk-rock,” but it taps into several genres, at times churning out the kind of blues-rock Bonnie Raitt does best and at others serving up fare better-suited for Jack Johnson. Catch the M.C. Taylor-fronted group at the 9:30 Club. Doors 7 p.m. $20. All ages, accessible venue.
“Maybe love is overrated,” sings Beach Bunny vocalist Lili Trifilio in “Sports.” Obviously. The Chicago alt-rock outfit (who takes their coastal name pretty seriously) stops by Songbyrd. Show 8 p.m. $12-$14. All ages, inaccessible venue.
FRIDAY, DECEMBER 21
On 2018’s Collages, June Pastel—a dreamy rock project led by Baltimore musician Anthony Peña—invites listeners into a drowsy soundscape of guitar delay, spacey keyboards and ambient sounds, making the rules up as they go. Take it all in at Songbyrd. Show 8 p.m. $10. All ages, inaccessible venue.
Yes, you might head to Bethesda Blues and Jazz Supper Club this week to hear Grammy winning-vocalist Macy Gray sing her beloved unrequited-love pop anthem “I Try,” but you haven’t really heard it till it’s received a pared-down jazz treatment. Gray is uber talented, and not just because of her vocal chops or ability to craft relatable music—she’s also a dancer, a dramatic actress and, apparently, a comedian in this excruciatingly cringeworthy clip. Show 8 p.m. $67-$87. All ages, accessible venue.
NGHTMRE’s so hot right now, releasing collaborations with some of the biggest names in the music industry, from Wiz Khalifa to The Chainsmokers. See the L.A.-based DJ and producer at Echostage. Show 9 p.m. $25-$40. 18+, accessible venue.
SATURDAY, DECEMBER 22
Latin rock band Los Lobos may be best known for their rendition of “La Bamba” featured in the 1987 Ritchie Valens biopic of the same name, but we’d like to use this opportunity to highlight another film to which they lent their sound: 1995’s Desperado, starring none other than king of suave and former Melanie Griffith hubby Antonio Banderas. Enjoy this mariachi banger, later sampled in a track by rapper KRS-One, and see the band that started it all at City Winery (They’re also performing Friday). Show 8 p.m. $55-$70. All ages, accessible venue.
Indiana-based blues duo Left Lane Cruiser knows how to get down and get dirty. (By the way, that intro could totally segue into Fleetwood Mac’s “The Chain.”) Catch them at Hill Country Live. Show 9:30 p.m. $15. All ages, accessible venue.
D.C.-born jazz drummer-turned-Hollywood music producer Nate Jolley comes to Sotto. Show 8 p.m. $15. All ages.
SUNDAY, DECEMBER 23
Shy Glizzy is only in his mid-20s, but the D.C.-bred rapper has already forged a prodigious career in hip-hop, with several mixtapes and a new album on which he rap-sings, “I never been the type to live up to the hype/I promise, long as they print money I’ma be alright.” Throw him some dough at Echostage. Show 9 p.m. $30-$35. All ages, accessible venue.
Every year, artists from Josh Groban to Kelly Clarkson to TLC issue fresh takes on classic Christmas carols. And then there’s the Trans-Siberian Orchestra, who just annihilates them. Catch their dynamic Ghosts of Christmas Eve show at Capital One Arena. Show 8 p.m. $45-$79+. All ages, accessible venue.
MONDAY, DECEMBER 24
If by some miracle you haven’t hit your annual quota for holiday music by the time Christmas Eve hits, head over to the Kennedy Center Millennium Stage to hear The Beltway Brass Quintet. Show Noon. FREE. All ages, accessible venue.