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DRINK: Portland Elvis’ All-Star Xmas Eve Extravaganza
Portland Elvis’ decadeslong Portland karaoke tradition sees him perform all your favorite holiday tunes, accompanied by a lineup that includes Paul Brainard and his Fun Machine Orchestra, Steve Wilkinson & Dr. G, Paul Becker (Dry Country Crooks), Natalie Lucio (Bad Juju), Dan Eccles (Richmond Fontaine), Jenny Newtson, and Andy Stromstad (I Am the Intimidator), to name a few. This is a rare opportunity to give Santa a gift for a change—don’t miss out on those karmic good graces. Starday Tavern, 6517 SE Foster Road, stardaytavern.com. 5–9 pm Wednesday, Dec. 24. Free. 21+.
WATCH: Michael Harrison Christmas: Closing Night
Another beloved Portland holiday tradition is seeing Michael Allen Harrison’s Christmas at The Old Church. This show goes deeper than the expected full-throated choir and chest-swelling, bells-and-holly traditional fare. Instead, Harrison presents innovative, alt-Christmas arrangements featuring the legendary vocal talents of gospel, blues and jazz singer Julianne Johnson, as well as a full slate of talented young artists from our own creative community. The Old Church, 1422 SW 11th Ave., tocportland.org. 1 and 5 pm Wednesday, Dec. 24. $35–$65. All ages.
GO: McMenamins White Elephant Bingo at Kennedy School
Folks hankering for some old-fashioned community fun might want to drop in on a special Christmas edition of McMenamins Kennedy School bingo, with holiday-themed cocktail specials and goofy prizes for winners. Lower-tier prizes will be wrapped like presents—because Christmas—so you won’t know what you’ve won until after you’ve torn it open. The grand prize of each round is unwrappable: an overnight stay at the Kennedy School. P.S. No need to bring a gift; the presents are covered. McMenamins Kennedy School, 5736 NE 33rd Ave., mcmenamins.com. Noon–5 pm Thursday, Dec. 25. Free. All ages.
WATCH: Holiday Rehab
Wherever you sit on the holiday spectrum, this season can be hard. You, or someone you know, will likely need to do some intense emotional regulation post-Christmas. Where better to get that taken care of than at an iconic comedy show themed around rehabbing your way out of holiday purgatory? Bury your feelings under a burger and a beer, then let them out via laughter inspired by an elite squad of Portland’s funniest people, including Jordan Casner, Adam Pasi, Imani Denae, Virginia Jones and Don Gavitte. Mississippi Studios, 3939 N Mississippi Ave., mississippistudios.com. 6:30 pm Thursday, Dec. 26. $26, 21+.
WATCH: Shane Torres
Erstwhile Portlander Shane Torres returns to Stumptown for three nights of shows at Helium. A local favorite, his return demands some hometown love. For the uninitiated, catch Torres’ podcast, No Accounting for Taste with Kyle Kinane, wherever you get your podcasts, to sample the wares. Shane actively tours comedy clubs, concert venues, and some of the most prestigious festivals around the world. Helium, 1510 SE 9th Ave., portland.heliumcomedy.com. 7 and 9:15 pm Friday and Saturday, 7 pm Sunday, Dec. 26–28. $34–$46. 21+.
WATCH: Neon Rainbow
In the taint of the holiday season, it can be easy to become sucked into the eternal void of quickly depleting cheer. Perhaps find a panacea by reveling in the queer space created by Brendan Creecy as he hosts a showcase of Portland’s finest queer comedians, featuring Ally J. Ward, Imani Mack, Cody Webb, Colin Mattox and Nick Altishin. It’s dark as heck out here—indulge the Roy G. Biv for an hour; your dopamine receptors will thank you. Funhouse Lounge, 2432 SE 11th Ave., funhouselounge.com. 6:45 pm Saturday, Dec. 27. $12.50. 21+.
WATCH: A Charlie Brown Christmas Live
Catch this critically acclaimed, live-action holiday special with songs from the unforgettable musical score of legendary composer Vince Guaraldi. This Broadway-style extravaganza overtakes the Keller Auditorium with immersive sets, lighting, choreography, and colorful costumes, and has sold more than 300,000 tickets over prior holiday seasons. If that number is giving you FOMO, get your tickets now. Keller Auditorium, 222 SW Clay St., portland5.com. 3 pm Saturday, Dec. 27. $40–$100. All ages.
GO: Heatwave: Drag Kings N Things Revue
With quite a bit of winter still on the horizon, it stands to reason that sweaty nightclub vibes are a potential panacea to holiday fatigue and cold-weather isolation. So, if the spirit moves you, by all means check out Heatwave Drag & Burlesque’s Kings N Things Showcase at iconic show bar Darcelle XV and swoon over a cast of hot-blooded Drag Kings and more, all there to make you, ahem, sweat. Hosted by Wolfgang X. Darcelle XV Showplace, 208 NW 3rd Ave., darcellexv.com. 6 pm Sunday, Dec. 28. $17–$40. 21+.
WATCH: It’s Gonna Be Okay
It’s Gonna Be Okay is a free weekly comedy show in East Burn’s Tap Room, and considering the timing of this week’s show, it bears mentioning that winter is rough stuff—but damn if we’re not all in this dark-as-snot time together, and if we just hang in there, then it’s gonna be okay. The show features local and national acts, with lineups announced weekly on the show’s Facebook page. East Burn, 1800 E Burnside St., theeastburn.com. 6 pm Monday, Dec. 29. Free. 21+.
GO: Drag Extravaganza
RuPaul’s Drag Race alumnae Roxxxy Andrews and Anetra are here to make it clear that the New Year should start with good cheer, baby! Kharisma plays host duties with Lyta Blunt covering music (you know the stoner baddies of the House of Blunt will have those vibes handled in spades), leading a roster of local drag superstars, including Eris, Harlow Quinzel, Boujee Cherry and WW’s Finest Drag Artist winners Mona Chrome, Kimberly Michelle Westwood, and Tomboy. Star Theater, 13 NW 6th Ave., startheaterportland.com. 7 pm and 10:30 pm Wednesday, Dec. 31. $42.72–$88.04. 21+.
GO: 2nd Annual Pioneer Square New Year’s Eve Drone Show
Sure, you could ring in the new year in the warmth of your own home, or someone else’s, but what if you want to be outside and around strangers? More than 20,000 people braved the chilly weather and watched the cold light of LED drones flying in synchronized patterns last year, so the city of Portland is bringing the New Year’s Eve Drone Show back to Pioneer Square this year with a Video Dance Attack-hosted dance party, onsite food vendors, and remarks by Mayor Keith Wilson (LadyBerri Matthews, drag queen extraordinaire, should balance him out as the returning emcee). Pioneer Courthouse Square, 701 SW 6th Ave., thesquarepdx.org. 8 pm Wednesday, Dec. 31. Free. All ages.
GO: O-69 Comedy Bingo
If you resolved to eat better in 2026, remember that breakfast is (probably) the most important meal of the day—and breakfast for dinner counts, in our book. If you also resolved to laugh more, O-69 Comedy Bingo is the place to be. Over Easy Breakfast Bar kills all those birds for you and fries and scrambles eggs for your enjoyment as Portland comedy powerhouse Andie Main hosts a New Year’s Day edition of bingo, big jokes and breakfast platters. However you celebrated the previous night, O-69 probably has what the doctor ordered (unless the doctor ordered you to watch the fried foods, but the kitchen can likely go easy on you). Over Easy Bar and Breakfast, 6801 N Columbia Way, overeasy.bar. 7 pm Thursday, Jan. 1. Bingo cards $5, three for $10. 21+.
GO: 50 First Jokes
This showcase features Portland’s emerging and established comedians who haven’t taken to a stage since, like, 2025. They’re ready to show off the freshest material of the year, as Jordan Casner leads a roster of 49 other comedians to share the first jokes they’ve written for 2026. Topical? You bet. Locked and loaded? Here’s hoping. This is a show for the trendsetters who want to know what’s at the top of everyone’s mind with last year’s slate formally wiped clean. Mississippi Studios, 3939 N Mississippi Ave., mississippistudios.com. 9 pm Friday, Jan. 2. $22.20. 21+.
GO: Vision Euro Söng Cöntest
Whether you’ve always been a fan of Eurovision or started tuning in because of that fake news post announcing that Ke$ha would kuntenserven for the United States—despite the U.S. very famously not being a European country—Portland comedians Erika Lowe and David Gordon know you can’t wait until spring for schmaltzy Balkan ballads or Nordic bops. This improvised song contest lets the audience suggest topics for the songs that will fuel Portland comedians-slash-singers to the top of Europe’s pop charts. Portland Comedy Theater, 535 NW 16th Ave., portlandcomedy.com. 9 pm Saturday, Jan. 3. $15. 18+.
SEE: Up the Down Escalator by Gabriel Francis
Photographer and mixed-media artist Gabriel Francis spent last year developing work that shows people who are often overlooked by broader society due to factors like income, medical history, and cultural background. Along with gorgeously developed black-and-white portraits, Francis developed collages inspired by boarded-up windows and found art like bus stop poetry and other ephemera. Up the Down Escalator encourages viewers to slow down and reexamine the world around them, a good challenge to start the year off right. Franklin FOTO, 8953 N Lombard St., franklinfoto.org. 5–8 pm Saturday, Jan. 3. Free. All ages.
SEE: Domestic Topographies by Colin Kippen
Colin Kippen’s sculptural work is inspired by how everyday objects engage our bodies, particularly through support or safety, like how mattresses and oven mitts are, respectively, woven for our comfort and protection. Kippen uses concrete to reinterpret these textures, painting them in ways that make the viewer more aware of the daily rituals we take for granted, like sleeping or preparing or sharing meals. Though the exhibition’s reception is Jan. 10, it can be fun to be the first one to see art without hordes of people crowding around the work. Well Well Projects, 8371 N Interstate Ave., #1, wellwellprojects.com. Noon–5 pm Sunday, Jan. 4 (on view weekends through Feb. 1). Free. All ages.
GO: Crystal Ballroom History and Art Tour
Have you ever stared around the Crystal Ballroom, bouncing on that floating ballroom floor, and wondered what stories all the art could tell? McMenamins is ready to talk. The company will host four tours of the venue in January. McMenamins tour guides are typically very passionate about the history-rich properties their venues inhabit, so surely guests are in for some hot showbiz goss from the past century-plus as they learn about how the concert hall survived vice raids and the wear and tear of time. Crystal Ballroom, 1332 W Burnside St., crystalballroompdx.com. 10 am Jan. 4, 8, 15 and 18. $15, free for children 2 and under.
GO: Karaoke From Hell
If you saw the band’s namesake documentary in 2025 and were inspired to take part in more Old Portland traditions in 2026, then what better week to front a live karaoke band with your own pipes than the first Monday of the year? Karaoke From Hell has quite the genre-spanning repertoire to choose from, so surely they’ve got a song you can slay—and if not, they can at least generously play in whatever key you’re finding yourself hitting (no judgment). Dante’s, 350 W Burnside St., danteslive.com. 9 pm Monday, Jan. 5. $8.26. 21+.
LISTEN: Morgan Freeman Symphonic Blues Experience
The legend himself curated and narrates this immersive show spanning the history of Mississippi Delta blues music, to be executed by the Oregon Symphony. Freeman’s voice guides a program of 20th and 21st century blues essentials that will surely be part cinematic storytelling and part stirring concert. While the actor’s mesmerizing voice is an instrument in its own right (even if his attendance is not guaranteed), Freeman’s selection of songs will be an artful flex of his musical taste and knowledge we’re still blessed to hear. Arlene Schnitzer Concert Hall, 1037 SW Broadway, portland5.com/arlene-schnitzer-concert-hall. 7:30 pm Tuesday, Jan. 6. $48–$122. All ages.
