[Read all of the articles in our Portland Fun Guide HERE! Looking for a print copy? Look at this handy-dandy map!—eds.]

Portland needs a Medieval Times. Like, what city would get MORE into the idea of swigging ale, chomping a turkey leg, and watching people joust in period specific costumes? Feels right up our alley. That being said, there are plenty of super fun options to eat a fine meal while watching a show—be it comedy, jazz, or just a good movie. There may not be any performative horsemanship, but drag queens doing death drops is a lot more fun anyway.

The 1905

If there were one spot I’d recommend for dinner and a show, The 1905 is it. Just off Mississippi Avenue, this cozy little jazz club offers a primo lineup of local and touring artists, like a monthly bossa nova night and experimental quartets. Even better, the cocktails and food are destination worthy on their own.

For the last year, former Italian pop-up Scorfana has been running the kitchen at The 1905, with basics like a slice of cheese pizza, to elaborate specials like roasted game hen with pickled cherry bombs and jus, or a shaved fennel salad bursting with acidic dressing and sweet muscat grapes. The spaghetti and meatballs offer three substantial meatballs in a salty (good salty) marinara, excellent for sharing with your date. Shows sell out, so make sure you reserve a good table well in advance—and if you’re in the front row, you could even offer a bite to the bass player sitting just a few feet away.

830 N Shaver, the1905jazz.club

Darcelle XV Showplace

Darcelle may have passed in 2023 (Darcelle forever), but her spirit lives on at her nightclub. It’s unclear if you can truly call yourself a Portlander if you haven’t spent at least one night at the nation’s oldest drag club, downing vodkas, and (OF COURSE) raining the performers in fresh dollar bills. Darcelle shows are raucous, a little raunchy, and naturally 21-plus.

These days, there are Friday and Saturday night shows, and a Sunday brunch. While the food is far from remarkable, you can’t really mess up chicken tendies and burgers, and nothing on the menu is more than $13, which leaves you more dough to hand over to the dolls.

208 NW 3rd, darcellexv.com

McMenamin’s St. John’s Pub and Theater

Portland may have the highest ratio of strip clubs per person in the US, but I’m guessing our independent theater ratio is way the hell up there too. While many theaters have fantastic pizza and popcorn options, McMenamin's St. John’s Pub and Theater is the move if you’re looking to really nosh while consuming cinema.

First run shows are just $9, and splitting a basket of cajun tots while watching Robert Pattinson die multiple times during Mickey 17 is a real delight. The St. John theater also has tables for every row, a soaring peaked ceiling, and eerily good surround sound. Sure, stanning a McMenamin’s is a little cringe, but sometimes it’s just the (movie) ticket.

8203 N Ivanhoe, mcmenamins.com/st-johns-theater-pub

Karaoke from Hell at Dante’s

Every Monday at Dante’s the dinner show is YOU. That’s when they rev up the longstanding Karaoke from Hell, where wannabe Micks and Mariahs have the chance to sing their song of choice in front of a live band. Five bucks gets you in the door, but have cash on hand to tip if you want to secure a slot. 

Don’t worry, you’re not spending big on dinner here—a couple of NY-style pizza slices from the window attached to Dante’s will do just fine. Even if you don’t have the cojones to sing live yourself, watching someone drunkenly fuck up “Welcome to the Jungle” while munching on a piece of pepperoni sounds like a pretty nice little Monday, if you ask me.

350 W Burnside, danteslive.com

Funhouse Lounge

Portland be Portlanding at the Funhouse Lounge, self-described as a fringe theater, clown room, and arts venue. There are regular standup showcases, along with a roster of improv comedy shows that can get real weird, and real funny. Look for the annual USS Improvise: The Next Generation: The Musical, or DomProv, a late night show where a dominatrix has the improvisers do her bidding.

Food is a basic pizza/nacho business, but if you reserve a booth, they’re also cool with you bringing in food from the outside–and you’re real close to all the bounty Southeast Division has to offer. Try not to get anything you can blow out your nose while laughing.

2432 SE 11th, funhouselounge.com

Live Music at the Bar at Clyde’s Prime Rib

Clyde’s restaurant first opened its doors in 1955, and there’s no better place to soak in their midcentury cool than in the bar. Put on your best go-go boots and sip a martini while you take in acts like Bridge City Soul and the Executive Groove Band. 

Live music happens every Friday to Sunday, and it pairs best with the prime rib bites, smothered in horseradish and au jus, and a classic creamed spinach, with plenty of garlic butter toast to dip in it. It’s enough to make you wish we could still smoke inside.

5474 NE Sandy, clydesprimerib.com