When it opened 90 years ago this week, it’s a safe bet that nobody expected Portland’s Eastland Hotel to become famous for two things: a red-lettered sign punching its cocky closed caption through the city’s skyline, and an ironically tenuous sense of its own identity.

The historic Arts District hotel, now the Westin Portland Harborview, has had some ups and a generous share of downs. But through several tough decades, it found a way to survive by aligning with a Zsa Zsa-esque string of partners. Once it was a Sheraton, later a Sonesta, a Radisson, and today it is part of the Starwood group. Change is as much a part of the hotel’s DNA as its iconic sign.

It also never seems to stop. As recently as four years ago, the rooftop lounge, Top of the East, was gutted and remodeled, losing elderly furnishings while adding two times the square footage and new floor-to-ceiling windows that overlook the town. With chill-out music playing overhead, a gargantuan wall-mounted television and filament-style LED Edison bulbs mounted naked in a grid pattern across the ceiling, the room feels nothing like it must have when it opened in 1963.

But even with some welcome updates, it’s still not clear exactly what the space wants to be. Among the satin pillows and blocky, modern sofas are round, tempered glass tables and inexpensive-looking rectangular four-tops that resemble a style of bland, indestructible conference center decor that was popular 20 years ago. A chrome-rimmed communal table looks as if it was stolen from the set of an ’80s sitcom. The view may be even more panoramic than before, but the room does not seem to understand its own era.

The cocktail list doesn’t help. With a focus on what Brian Anderson, executive chef and director of food and beverage for the hotel, describes as “classic cocktails in a modern lounge with a 1960s, 1970s feel,” the drinks seem as mismatched as the interior design. The High Street Sidecar ($13) – made with rum in place of cognac, along with Grand Marnier and lime juice – is a sweet-tart pleasure to drink, even though the substitution actually makes it a daiquiri. Then there’s the Cynar margarita ($15), a drink that tweaks tradition with bitter, artichoke-based Italian amaro. It’s a classy, layered cocktail perfect for slow-sipping: totally on-trend for 2017, yet at odds with the classic theme of the list.

The menu, while generally focused on small, shareable plates with just a few larger-format options, further confuses any sense of cohesion. There are contemporary appetizers like weirdly sweet-tasting chipotle-spiced deviled eggs ($11), enriched with crème fraîche and served in an indented, egg carton-like plate that makes retrieving them a slippery chore. Or dry, oversized and oversalted bacon meatloaf sliders ($14) on panini-pressed brioche buns. If you weren’t thirsty enough to order one of the lounge’s pricey cocktails when you walked in, a few bites of either of these dishes will solve that problem.

These issues echo many of those identified in 2011, in a three-star review in this paper. Our then-reviewer praised some of the cocktails, but flagged the lack of balance and technique in many of what she described as “underwhelming choices” among the overpriced, lackluster small plates.

Shift to the larger dishes on offer today, though, and you start to see Top of the East’s promise. The seared yellowfin tuna entrée ($23) turns out to be a chilled, artfully deconstructed salade niçoise, with bitter frisée, blanched asparagus tips and sushi-grade tuna sourced from Harbor Fish Market. It’s all brought together by a lively tomato vinaigrette striped onto the plate with heavy impasto. The dish looks and tastes like the kind of plate you’d expect to be served on the rooftop of a swank historic hotel.

The 16-hour short rib ($19) is even better. Anderson and his team sear the beef and cook it slowly at 220 degrees F for just shy of a full day, then reduce the juices into a thick glaze and serve the rib over roasted root vegetables. “It’s the same concept as a pot roast,” Anderson said. But sprinkled with a crunchy, savory rosemary breadcrumb topping and plated with a bittersweet tangle of microgreens, this tender roast brings together high and low elements with deftness and finesse.

The classy Cynar margarita. Staff photo by Shawn Patrick Ouellette

Nevertheless, Top of the East struggles to maintain an aura of sophistication in more than just fits and starts. I visited twice over the past month. On the first visit, during a clear night when you could sit and watch what seemed like every wharf and jetty in the harbor, the lounge was jumping and service was brusque. “If you really have to sit by a window, you can just push the dirty glasses to the side, and someone will probably come get them,” a server told me. On another visit, a foggy evening when I had to squint to make out the contours of Robert Indiana’s “Seven” sculpture across the street, things were a lot quieter. Yet an unoccupied neighboring table sat with dirty glasses and dishes uncleared for more than half an hour.

Those new LED bulbs, while trendy and warm, cause a few problems of their own. The color value of the light washes out food, making greens look muted and reds look brown; even with intelligent, creative plating, dishes never look as good as they should. The lights also produce a distracting high-frequency flicker. It’s not bad enough to cause a Pokémon cartoon seizure, but it does create a strobing effect you can see when you move your hands. And when booze is in the picture, fewer unsettling visuals are always best.

It’s almost as if there’s a conspiracy afoot to encourage patrons to look out the windows and ignore what’s inside Top of the East: décor, service and much of the menu. That stratagem works when it’s nice outside, but what happens when the weather does not cooperate? The solid cocktails are a good place to start, but it’s clear that stronger cooking is where the restaurant’s next evolution needs to be. Brian Anderson said it himself when describing the how he would like to see things progress: “We don’t want to overwhelm Top of the East with food, and we don’t want to make food the focus, but we do want it to be able to stand up next to the drinks.” Right now, that mission remains only half-accomplished, but it’s a change worth making.

Andrew Ross has written about food in the United Kingdom and in New York, where he co-founded NYCnosh, a food website. He and his work have been featured on Martha Stewart Living Radio and in The New York Times. He is an Internet researcher and higher education consultant. Contact him at:

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Twitter: @AndrewRossME