Winky Dinky Dogs opens in Oakland’s former Original Kasper’s triangle

“This is not your average hot-dog stand. You know what this is? This is Winky Dinky Dog!”

This line from the classic 1980s comedy “Hollywood Shuffle” has become reality in Oakland’s Temescal neighborhood. On Jan. 24, Winky Dinky Dogs opened its long-awaited spot at Telegraph Avenue and 46th Street, turning a historic and curiously shaped building into a dispensary for hot dogs, fried ribs, gumbo and “wangs.”

It’s the second Winky Dinky Dogs in Oakland — and perhaps just one in an impending avalanche of Winky Dinkies to hit the Bay Area, more on that in a minute – for owner and local entrepreneur Tyranny Allen.

“It’s been a long process, but we’re finally open, and the community has embraced us,” Allen said. “We’ve been pushing a thousand hot dogs a day, even right now as we speak.”

Allen is known in the community as being part of the legendary hip-hop group The Digital Underground. His second career as a restaurateur appears to be taking off. Aside from his Winkies, in late 2025 he also opened the Bread Winners sandwich shop in Oakland’s Swan’s Market. (He also owns the city’s Lucky’s Barber Shop.)

For Allen, selling hot dogs is almost a muscle memory. “Winky Dinky Dogs started off right here in Oakland,” he said. “I started off like my Mexican brothers, pushing a (hot-dog) cart. I still got, like, eight carts.”

The eatery has moved into a building that fittingly has a tubular past. Since the 1940s, it was home to Original Kasper’s Hot Dogs, a local institution that moved out in 2003. The triangle-shaped structure, which viewed from above looks like a pizza slice, attracted graffiti and even an art show devoted to its ever-changing facade before Allen bought it in 2025.

Whereas Kasper’s sold Chicago-style dogs, Winky Dinky’s “Original Dog” is a choice of a beef, chicken, pork or vegan filled dog with peppers, onions and mayonnaise. There’s a chili dog, a “Mistah F.A.B. Mac N Chz Dog” named for the Oakland rapper and a “World Famous” with bacon and cherry peppers. That’s just the tip of the menu offerings, though.

There are chicken sandwiches with red-hot ranch, a smashburger called the “MC Hammer,” “Beastmode Loaded Fries,” fried pork ribs and “Winky Dinky Wangs” in flavors of sweet-hot, garlic-pepper or Parmesan. Later this winter, the location is expected to receive its liquor license and will sell wine and draft beer.

“And don’t forget we got the best gumbo and oxtail in Oakland,” Allen added.

All this comes from a restaurant that barely looks big enough to hold its kitchen staff — it’s perhaps five hot dogs wide at its narrowest, to use a relevant measure — though diners have the option to eat outside on a sidewalk patio. And sports fans should take note: This patio will be the site of a Super Bowl celebration on Feb. 8 featuring two 90-inch screens.

The Bay Area soon will be saying “Winky Dinky Dogs” a whole lot more, if Allen gets his way. His team is planning to expand within the year to Walnut Creek, and beyond that he believes the world’s his oyster … er, processed-meat tube.

“We’re going to be doubling. Every four to six months we are planning to sign a new lease in prospective cities,” he said. “We’re looking at Walnut Creek for our next goal. And we’re already negotiating to go out to Dublin, Sacramento and San Jose.”

Details: Open 11 a.m.-8 p.m. daily (hours might change upon receipt of liquor license) at 4521 Telegraph Ave., Oakland; winkydinkydogs.com