Kickin’ It Old School

There’s no shame in aiming higher than Pabst and cheese fries. Remember back when Cary Grant charmed Grace Kelly in To Catch a Thief? When a dinner jacket and freshly shined kicks were just as crucial to an enchanted evening as the first sip of a martini? Gentlemen, scare up some cuff links. Ladies, steam your flimsiest silk dress. Tonight’s word is “debonair.”



What you’re drinking: A brandy alexander
There’s no shortage of joints in this town that try to tap into the elusive Rat Pack swagger of the Stork Club in its heyday, but Tony Starlight’s has a distinct advantage—namely, the presence of the dapper proprietor himself. He’s the hepcat, dressed sharp enough to slice cheddar, who materializes at your table inquiring about the quality of your cocktail, Daddy-O. Indeed, nothing can touch the twice-nightly Saturday stage shows when Starlight (forever sweatin’ to the oldies) keeps clusters of smartly attired diners rapt with a barrage of banter, jokes cribbed from Henny Youngman and a set list of swingin’ tunes that will have you wishing you’d paid more attention when Mom and Dad tried to teach you the foxtrot. (3728 NE Sandy Blvd, 503-517-8584)

What you’re drinking: A Spanish coffee
As if the dark wood and art-deco tile work weren’t clue enough that you’ve just stepped into the oldest bar in town, there’s the distant aroma of mustache wax lingering like ghostly potpourri. As befits a gentlemen’s club, there are no ill-trained drink monkeys on the premises. Instead, roving mixologists whip up flaming Spanish coffees with the flourish of magicians performing sleight of hand. A round of applause won’t embarrass anyone. (411 SW Third Ave, 503-228-5686)

What you’re drinking: A shot of Laphroaig
Battle your way to the bar of this bustling saloon; request a Blanton’s bourbon, neat. As the barkeep wheels his ladder in front of a 15-foot-tall tower of bottles to reach your brand, it’s hard not to experience a moment of awe: Cripes, that’s a load of hooch. Nearby, knots of business-casual types spill their workaday woes. But the sound of that ladder rolling from one shelf to the next keeps your white collar cooled. (65 SW Yamhill St, 503-224-5626)

What you’re drinking: A sidecar
The new bartender introduces himself as Burt and fashions a breathtaking martini just before pouring a respectable pinot noir for a grumbling Blazers fan. No small news, the arrival of Burt: A fresh face behind the stick at the Ringside doesn’t appear too often—bartenders here tend to have careers longer than Andy Rooney’s. But like his predecessors, Burt is Fred Astaire-smooth and calm as the Buddha, even when things get hopping. (2165 W Burnside St, 503-223-1513)