Former ‘Simpsons’ Writer and Fast-Food Influencer Bill Oakley’s Top Three Portland Diner Sandwiches

Bill Oakley — former Simpsons writer, fast-food enthusiast, snack food critic, patriarch of the Steamed Hams Society — knows his way around a drive-thru. But when it comes to Portland diners, he is hesitant to speak with too much authority. “What even constitutes a diner in Portland, you know?” he says. “The definition of diner has to be expanded.”

This theme has come up again and again as Eater Portland has prepared for Diner Land USA, a multi-city project in which Eater sites investigate and celebrate the dishes and phenomena encountered at their city’s diners. The quintessential Midwestern or East Coast diner, a chrome-and-tile-lined, midcentury greasy spoon modeled after a dining car, is less common in Portland. Instead, the city has several diner-esque spots: dive bars slinging pancakes, cafes with chicken-fried steaks, family restaurants with pie cases. Certain diner tropes appear at these spots — ’50s nostalgic aesthetics, milkshakes in a fountain glass, steak and eggs, short stacks — but it’s not a given that each spot hits every line item.

So, when we asked Oakley to share his diner standbys, he noted three favorite dishes found at classic Portland spots within the larger diner realm. Oakley, who has inspired at least one Portland sandwich, is a connoisseur of burgers, double-deckers, and melts, so his list sticks to wonders found between buns and bread. For more Bill Oakley picks, feel free to peruse his larger Portland dining guide. This interview has been edited and condensed for clarity.

Club Sandwich, Fuller’s Coffee Shop

136 NW 9th Avenue. Note: Fuller’s is currently finishing repairs after a fire; it should reopen June 23.

“I love chicken salad sandwiches, and it’s one of the best sandwiches I’ve ever eaten. Bobbie of Bobbie’s Boat Sauce told me about that sandwich, and it lived up to the hype. It seems like such a no-brainer, the idea of combining a club sandwich with a chicken salad sandwich. It works on every level, and I’m shocked I’ve never seen it anywhere else. Most club sandwiches are too dry, unless they’re slathered with mayonnaise — which the chicken salad addresses. You get the hot and the cold, the crunchy and the squishy, and I like that contrast of flavors.”

Cheeseburger, Jim Dandy Drive-In

9626 NE Sandy Blvd

“Jim Dandy is this weird relic — very, very old school, very working class, not at all connected to what we think of as urban Portland. And when we did that Portland Monthly cheeseburger survey, that was the best old-school cheeseburger I had. I would suspect that they’re not using any fancy ingredients; it’s probably a frozen burger cooked up on a grill. But it has a certain flavor, and a burger-y, Big Mac-y sauce that I recall really enjoying. It’s just a perfect execution of a diner burger. And, that coupled with the history of the place, all the memorabilia from the drag race scene, that’s a part of Portland you don’t see anymore. That place really brings it with the decor, the vibe, and it feels like it’s been going strong for 70 years or more, without needing any press.”

Meatloaf Sandwich, Sckavone’s Restaurant

4100 SE Division Street

“Sckavone’s Restaurant is one of those old-school places, and the meatloaf sandwich is excellent; I think that’s their signature dish. I’m a sucker for any meatloaf sandwich, but the combination of ingredients in this meatloaf, I don’t know what is in there. I’m sure there are some chopped up vegetables, green onions — you don’t get many meatloaf sandwiches really at all anymore.”

Bill Oakley is a former show-runner and head writer of “The Simpsons,” best known for writing the much-memed “Steamed Hams” segment. His hobby is making funny Instagram food reviews (@thatbilloakley) which have earned him the monicker “The Gordon Ramsay of Fast Food.”