Michelle Nelson has owned the diner since 1999; previous owners have included Benny and Phyllis Lum, as well as Ken Hom, who eliminated drive-in service.

[5] KOIN has described Skyline as an "iconic drive-in diner that has been serving Portlanders by the thousands every year for the past seven decades".

[10] The Portland Mercury has described the clientele as a "cross-section of high school kids and families, travelers, and even leather-clad couples roadtripping on Harleys".

[11] In 2001, Willamette Week's Jim Dixon said of the interior: "There's an espresso hut tacked onto the Cornell Road side to service the stream of commuters that pours by every morning and an ATM inside...

He also wrote, "Wood paneling, acoustic tile ceiling, and those Jetson-y light fixtures from the days of Sputnik provide a fitting setting for food that might have been transported from the Kennedy era as well.

The menu also included fish and chips with coleslaw, fried chicken,[11] hot dogs, tuna melt sandwiches, chili, and a Cobb salad.

There are two dozen float, malt, and milkshake varieties,[13] including banana, butterscotch, caramel apple, chocolate-covered cherry, hazelnut, marionberry, mocha, peanut butter, peppermint, and pineapple.

She described booths with black cushions, white formica tables, copies of a column written by American chef James Beard on display, and 1950s popular music in the background.

Amsden noted, "At 800 feet elevation, the Skyliner closes for three weeks every winter to give employees vacations when severe weather often affects business.

Sometimes it closes two or three times in winter months when snow or freezing rain becomes too severe for car travel on the roads winding up and down the hillside.

[20][21][22] Skyline was also impacted by Portland General Electric's temporary public safety power shutoff in September 2022, the result of high risk fire conditions.

[38] In her 2014 book Portland: A Food Biography, Heather Arndt Anderson said Skyline's burgers and shakes "are a testament to the utter pointlessness of reinventing the wheel".

[5] In 2022, writers for the website called the diner "the ideal spot for a weekend lunch" after hiking in Forest Park.

[11]Amara opined, "While it may be a blueprint for neo-nostalgia places like Johnny Rockets and Ruby's, Skyline is not a kitschy museum of '50s pop culture.

"[11] Following Food Network Magazine's recognition of Skyline's burger, Grant Butler of The Oregonian disagreed and wondered how research was completed.