Once upon a time, on “the neon trail” of Grand Avenue, there were six piano bars where patrons could gather ’round the piano and sing popular songs of the day. The Alley, the last one standing, is the third oldest bar in Oakland. It’s got quite a history and is known far and wide, said Jacqualine Simpkins, owner since 2009.

“We get visitors here from Europe now,” she said, “We’re listed in guidebooks.”

If you haven’t yet been to The Alley, it’s high time you did. The place has been around since 18-year-old rookie Joe DiMaggio’s 61-game hitting streak with the San Francisco Seals came to an end in 1933.

The Alley is actually a restaurant that serves alcohol; because of its cabaret license, The Alley has always made good use of the efficient kitchen in the back. An ad in The Oakland Tribune, dated 1954, says: “Open Every Day for Food and Cocktails, Very Little Waiting for Tables. $1 includes choice of 8-ounce Dinner Steak or Ground Sirloin, includes Salad, Potato and Garlic Bread.” The steaks are more than a dollar these days, but the menu lists several cuts, as well as fried chicken.

The piano bar at The Alley. Photo: Risa Nye
The piano bar at The Alley. Photo: Risa Nye

Most people come to The Alley to have drinks and to sing, however. The singing has been part of The Alley’s attraction from the beginning. Part of the “Golden Age of Radio,” there were live performances broadcast on Sunday mornings from 1946-1948. Ella Fitzgerald and Merv Griffin (on piano) performed at The Alley, as did many stars of the day including Peggy Lee, Lionel Hampton, Donald O’Connor, Eddie “Bozo” Miller (a singer, but well known back in the day as an “oyster-eating record holder”), Sally Rand, Stan Kenton and the casts of several Broadway shows, among many others.

The Oakland Main Branch’s History Room has a folder full of yellowed clippings labeled “Bars and Saloons,” which includes a treasure trove of articles about the joint, some dating back to the 1950s. One of the old-style write-ups from The Oakland Tribune, dated June 9, 1954, describes the Alley as “the most Bohemian bistro in the whole Bay Area,” and, “our most mature nitery; started back in ’34 a few days after repeal [of Prohibition]. The present owners are two Oakland gals: Maggie Williams and Jody Kerr…. This is one of the ‘dollar steak’ spots of the neighborhood.” The blurb ends with: “And next time you want to get off the beaten path… try The Alley and tell Mag and Jo I sentcha.” You can almost hear the clatter of keys from an old Royal typewriter.

Betty Marvin, Oakland’s Historic Preservation planner, shared The Alley’s application for City of Oakland Heritage Property status. These documents highlight the unique structure and history of The Alley. Although the building at 3325 Grand Ave. was built as a private residence in 1920, the bar opened as The Grand Alley Café in 1933 and went through a remodel the next year, designed by architect Francis Harvey Slocombe, whose other work (such as The Little Chapel of the Flowers and other structures of the Period Revival and Moderne styles) can be found in Berkeley and elsewhere.

The Alley, a self-described "ramshackle roadhouse" has an interior designed to look like a real alley.
The Alley, a self-described “ramshackle roadhouse” has an interior designed to look like a real alley. Photo: Risa Nye

In the application, the style of the building’s façade is described as “Berkeley Eclectic, with a carefully designed ramshackle roadhouse look.” The interior was designed to look like a real alley. Other design elements listed in this document reference the DeLancey Street bar in New York City, “right down to the ‘Alley Loan Company’ fake window, a woman’s silhouette at another fake window, lingerie on a clothesline, and a shack around the classic wooden bar.” Also, as noted: “the wallpaper is 9000 business cards, pictures, old playbills, and memorabilia contributed by patrons as a way of saying, ‘I was here.’” Today, it looks as though 9,000 is an extreme undercount, with thousands of cards stapled, stuck and push-pinned to the walls.

Other facts of note: in 1954 the upright piano was replaced with a baby grand. Verdi Carpenter, the “piano man” at the time, had “70,000 songs in filing cabinets.” Also: “veterans from Oak Knoll Naval Hospital came to The Alley for a free drink or the Hollywood breakfast: a black coffee, a cigarette, and a Bromo Seltzer for 25 cents.” What a bargain!

The Alley’s main claim to fame is “its association and preservation of piano bar music and from the many famous patrons who visited to play, sing, leave a business card or enjoy a drink.” What’s the attraction of the piano bar? Back in 1964, trend watcher Bill Rice told a Tribune reporter: “Few people want to sit around and just listen anymore.” At The Alley “people come in and grab the mike from the entertainer and sing themselves. They don’t sing good; but they’re happy.” (Full disclosure: Several years ago, this reporter had the honor of singing at The Alley’s piano bar. I was happy but did not “sing good.”)

A slightly more formal tradition continues at The Alley (patrons these days do not just grab the mic), even after long-time accompanist and maestro Rod Dibble passed away in 2017 at age 85. He began his gig at The Alley in 1960 and single-handedly kept the Great American songbook alive and well in the East Bay. Dibble and some of the regulars were the subject of a documentary, The Alley Cats (2012), directed by Cary Virtue. One scene in the recent film Blindspotting takes place outside The Alley. Today, patrons have the option of singing at a guitar bar with Paul Hlebcar or the piano bar with Bryan Seet or Jef Labes. Stools surround the piano and those desiring to belt out a tune take turns with the other songbirds gathered around. The Alley also hosts karaoke and trivia on different nights.

Owner Simpkins says the clientele has always been a mixture of all age groups, ranging from 21 to 80. Although the times have changed, The Alley has really not: the music, the “ramshackle roadhouse” vibe and the newest batch of business cards that relay the message “I was here.” As Simpkins wrote in support of Historic Property status for her beloved Alley: “There is something charming and comforting, even mysterious, about the retro ambiance of a bar frozen in time when modern life proceeds faster and faster.”

Avatar photo

Freelancer Risa Nye is a Bay Area native. She was born in San Francisco and grew up in the East Bay. She spent many happy years on the UC Berkeley campus, both as a student and as an employee. She has...