This was the question I recently contemplated while sipping a perfectly poured martini (gin, lemon twist) at the ‘21’ Club bar. It’s not purely nostalgia for one’s own past—looking around, the room skewed relatively young, and I wondered how many of these revelers were aware of the restaurant’s storied past and speakeasy roots. It might have had something to do with the décor, with its dark, lovingly preserved, clubby woodwork and an elaborate mosaic of tchotchkes suspended from the ceiling.

Certainly, the drinks come into play: A great classic martini bar must have great martinis, as well as historic appeal. Or perhaps there’s another, more intangible appeal.

From the Grand Central Oyster Bar, built in 1913, to Denver’s wine bottle-shaped Cruise Room, which opened the day after Prohibition was repealed in 1933, these bars and restaurants allow guests to drink while imaging all the other elbows once propped up on that same bar. Some are famous for hosting the famous and powerful at their tables (Musso & Frank, Big 4, ‘21’ Club); others offer fascinating architectural details (Shuckers, The Matchbox) or a taste of drinking in decades past (Gibson, Avery Bar). What brings people back to these bars, year after year?

The bartender at the ‘21’ Club, an older gent with twinkly eyes, leaned across the bar to offer this sage response: “People come to tip their glass to the past.”

Seek out these classic bars, and raise a glass to those who have come before us.

Most notorious for its role as a speakeasy during the Prohibition years, the ‘21’ Club recently added a front bar to serve the same powerfully chilled martinis, straight up or on the rocks, sipped at the “power tables” in the back.

‘21’ Club, New York, NY
21 W 52nd St, New York, NY
(212) 582-7200

Set in a clubby, mid-century-style lounge with a fireplace, the Avery Bar offers a selection of 10 martini variations, including “Fire” (with a jalapeño-stuffed olive), “Smoky” (with a rinse of Lagavulin Scotch) and “Russian” (with vodka).

Avery Bar, Ritz Carlton Hotel, Boston, MA
15 Arlington St., Boston, MA
(617) 574-7100

One of the few reservations-only bars in the area, with zero signage to help you find the unmarked door, this cozy, candle-lit bar is as close as you can get to speakeasy-style sipping in the modern world.

The Gibson, Washington, DC
2009 14th Street NW, Washington, DC
(202) 232-2156

This Nob Hill icon within the Huntington Hotel is named for “The Big Four,” the businessmen and philanthropists who built the Central Pacific Railroad. The powerful (and wannabe powerful) still come to sip a Martinez or a James Bond-style Vesper.

Big 4, San Francisco, CA
1075 California St., San Francisco, CA
(415) 771-1140

Open since 1938, Bryant’s is officially Milwaukee’s oldest cocktail lounge—it’s also arguably one of the most dimly-lit. Best bet is to order your martini during happy hour, which offers a special price on “Depression-era drinks.”

Bryant’s Cocktail Lounge, Milwaukee, WI
1579 S. 9th Street, Milwaukee, WI
(414) 383-2620

Located inside The Oxford Hotel, Denver’s first post-Prohibition bar (opened literally the day after Repeal in 1933), this art-deco stunner is an exact replica of a bar on the Queen Mary. It’s also shaped like a wine bottle.

The Cruise Room, Denver, CO
1600 17th Street, Denver, CO
(303) 628-5400

When Grand Central Terminal opened in 1913, this landmark seafooder opened along with it, and managed to survive bankruptcy in the 1970s and a fire in the late 1990s. Order “Oyster Bar-Tinis” made with vodka or gin (or select from the substantial wine list) to wash down a platter of mollusks as you admire the archways and Gustavino tiled ceilings.

Grand Central Oyster Bar, New York, NY
Grand Central Terminal, lower level
89 E. 42nd St., New York, NY
(212) 490-6650

This aptly-named, pint-sized bar with a mere 18 seats has stood for more than 75 years, and some say the drink offerings—stiff and icy-cold—haven’t changed much. Though the space is small, the drinks are oversized, which is excellent compensation.

The Matchbox, Chicago, IL
768 N. Milwaukee, Chicago, IL
(312) 666-9322

So Old Hollywood it hurts (supposedly execs would come here to peruse scripts over an icy martini). Bartenders with decades of experience still turn out the ‘tinis, with extra presented in a sidecar set in ice.

Musso & Frank Grill, Los Angeles, CA
6667 Hollywood Blvd, Los Angeles, CA
(323) 467-7788

Oysters and crisp, cold gin martinis are a perfect pairing at one of Seattle’s oldest oyster bars, located within the Fairmont Hotel. Squint and it’s still the 1930s, thanks to the cozy, dark carved-oak paneling and pressed-tin ceiling original to the haberdashers that once inhabited the space.

Shuckers Oyster Bar, Seattle, WA
411 University Street, Seattle, WA
(206) 621-1984