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Portland City Grill
111 SW 5th Ave., 503-450-0030, portlandcitygrill.com. 4-7 pm and 9 pm-close Monday-Saturday, noon-close Sunday.
[UPPER DECK] This steak house sits atop Big Pink, Portland’s most voluminous office tower, with expansive views of the city and surrounds. It’s a place the bridge-and-tunnel crowd goes for anniversary dinners, and likely to strike central city snobs as an upscale Outback. But the happy hour here is not just a time-honored tradition, but probably something to add to your Portland bucket list. Get there promptly at 4 pm to snatch a window seat or sit enviously on the interior. The kung pao calamari ($9.95 for a heaping portion) is a longtime fave, but we preferred the steak sandwich (also $9.95) and the Caesar salad ($5.95). Beer and cocktails pretty much go for street prices ($4.75 for Coors Light, $5.75 for a craft pint, $9.75 for a Scofflaw with top-shelf bourbon). You’ll notice that the pros in the windows mostly opt to split a bottle of wine ($26). MARTIN CIZMAR.
Best deal: Curry fried fish and chips ($7.95) and bottles of wine ($26).
Ringside Steakhouse
2165 W Burnside St., 503-223-1513, ringsidesteakhouse.com. 9:30 pm-close daily, 4-5:30 pm Sunday.
[THE ORIGINAL HAPPY HOUR] Long before there was Portland, before tribes settled in the Willamette and were wiped out by sickness, before mammoths, before the dinosaurs died, there was the RingSide happy hour. It was always here. It was the founding idea of Portland. It is our legacy to our children. It was my first “fancy” meal as an adult. It will probably be my last “fancy” meal when I’m an old and lonely cheapskate. And it is $4.75 for a heaping portion of steak bites. There are other deals—notably an excellent $5.75 prime rib French dip and a solid $3.75 hamburger whose price seems unreal—but always you are here for the steak bites, which are the trim bits of rich people’s meat priced just for you…the poor who like to feel rich sometimes. What a wonderful place, this parking-valet palace of Burnside that lets the poor feel rich, just for a little while. MATTHEW KORFHAGE.
Best deal: Steak bites. Burger. French dip. Mussels in pasta. Meatballs. Whatever, nothing’s over $6.
Sayler’s
10519 SE Stark St., 503-252-4171, saylers.com. 3-6 pm weekdays, 9 pm-close nightly.
[LOW STEAKS] Sayler’s Old Country Kitchen steak house is a sprawling East Portland meat hotel with loyal customers who go back longer than many of our readers have been alive. It advertises the best happy hour on the eastside—and it’s hard to argue when seemingly everything in the world costs less than $5 before 6 pm and after 9 —whether $3 wells and drafts, $2.95 onion rings or $4.95 peppersteak bites or chicken strips, with crazy old-time novelties like a $2.95 relish plate that turns out to be a crudité party tray of carrot, celery, baby corn, pickle and olive—complete with ranch. It’s cheaper than you’d get it at a grocery store. MATTHEW KORFHAGE.
Best deal: If you want to go really cheap, get the 72-ounce steak and eat the whole thing in an hour to get it for free. I did, anyway.
Willamette Week