Crowds gathered at the Flamingo recently to celebrate St. Petersburg’s “oldest bar with the longest original owner," as the sign displayed out front read.

Surely someone must have ordered the Kerouac special, a $2.50 “shot and a wash," meaning a whiskey and a plastic cup of beer. It’s named for Jack Kerouac, the legendary writer who drank there occasionally in his final days in 1969. It feels like not much has changed in the wood-paneled, smoke-kissed barroom since then.

But is the Flamingo the oldest bar in St. Petersburg? That all depends on how you measure.

Read more from tbt*'s ultimate bar guide:

Readers’ favorite bars and breweries

Tampa Bay brewery guide

Bartenders around the bay

Women in brewing

Tampa Bay’s most dynamic boutique distilleries

The Flamingo turns 50. Is it the oldest bar in St. Petersburg?

Taste sour beers at these tongue twisting taps

Boozy brunch

Mastry’s Bar opened on Central Avenue in 1936, though you could start the clock a bit earlier since the same owners had operated the Pink Elephant beer parlor at that same address in 1935. A story in this newspaper noted the new Mastry’s Bar and Grill would feature a luxury at the time: “air cooling."

But Mastry’s Bar, still owned today by the descendants of original owners John and Lay Mastry, moved to its current location at 233 Central Ave. in 1988, when the original bar was demolished to make way for a city parking garage. Start counting in 1936 and it’s definitely the oldest. Start the clock in ’88 and it’s a youthful 30, a mere millennial.

The interior of the original Mastry's Bar in St. Petersburg is seen in this 1937 ad from the then St. Petersburg Times. [ Tampa Bay Times ]

You could make a case for the Emerald Bar as oldest in town. That hazy cavern with the stone facade at 550 Central Ave. has been around in some form since at least 1945, when the “Emerald Inn” first appeared in the Times after the owner was fined $50 for selling booze to minors.

The lounge reappears in the newspaper in 1948 as the Emerald Bar, when the owner sued some local guys for $25,000 for “gossiping” about him and supposedly ruining his business.

George J. Marano, whose son still owns the Emerald, bought the bar in 1950, but he moved it across the street to its current home in 1964 to make way for yet another parking lot. At 55, the Emerald is just old enough to get a discounted “senior coffee” at McDonald’s.

Does it count if the place serves food? In that case, you could throw the Sunset Grille into the mix, formerly known as the Sunset Inn, or “Ben’s Sunset Inn," as it was called in a 1946 newspaper ad. But while you could certainly call Sunset Grille at 2996 Dr. Martin Luther King Jr. St. N a neighborhood dive bar, you also wouldn’t be faulted for calling it first and foremost a burger joint.

And then you’ve got the Flamingo, a business operating with the same name in the same building at 1230 Dr. Martin Luther King Jr. St. N since March 1937, when it opened as a drive-in restaurant selling wine, beer, ice cream and sandwiches. By the mid-1950s, according to permitting records, it had evolved from a concrete, open-air barbecue stand to an indoor spot. A Times story from 1955 is the first reference to the “Flamingo Bar.” It was the scene of a theft where the crook stole parts of a toilet.

References to the Flamingo having been in operation since 1924 appear to be a mixup with a different Flamingo restaurant, a jazzy spot that was “the home of mirth and frolics” according to newspaper ads, that operated a few blocks away on the same street.

A clipping from the St. Petersburg Times from Aug. 2, 1955. [ Tampa Bay Times ]

Does that make the Flamingo an octogenarian, or just approaching retirement age? The management went with an even more conservative number last week, throwing a 50th anniversary party.

Owner Dale Nichols bought the business in 1969, right after he got home from the Vietnam War to his native St. Petersburg, and so, in a way, it was really the 50th anniversary of Nichols. He came into the bar every day for decades, he said, even slept there plenty of times, though nowadays he takes an occasional vacation.

“I’ve never been able get away from Ninth Street,” he said, kicking back in a cushy barber chair in a corner of the bar. “I was born in a house on Ninth Street — people were born in houses then — just up the street from here.”

His big addition to the bar at the time were the pool tables, which were home, he said, to some legendary games with some legendary players over the years.

“Efren Reyes, Steve Mizerak, Charlie ‘The Tuna’ Jenkins,” Nichols said. “They all played here.”

“Detroit Whitey, Big Bob Osborne, Efren Reyes," added Gary Watson, a longtime regular seated in another nearby barber chair. “Some real good games. Too numerous to count.”

Nichols himself said he learned to shoot pool after he dropped out of school at 14 and began traveling throughout the South with a partner, looking for action on the outskirts of cities where big pool tournaments were happening.

Flamingo owner Dale Nichols bought the business in 1969, right after he got home from the Vietnam War to his native St. Petersburg. [ TIMES (2011) | Times (2011) ]

Asked if the bar had been a profitable business for him, Nichols glanced at a pool table, underneath a sign that read “No Gambling” in big letters.

“The worst thing that ever happened was credit cards," he said. “People didn’t carry much cash after that.”

The Flamingo, where you can get a $2 beer (perhaps plucked from a plastic cooler), or the mixed drink special (three of them for $6), remains steadfastly cash only.

These days, the bar is best known to nonregulars as a place where Jack Kerouac drank occasionally in his final days. Nichols used to hang out with the famous Beat generation writer sometimes, but Kerouac died at 47, only months after Nichols bought the place.

The Jack Kerouac mural outside the Flamingo bar at 1230 Dr. Martin Luther King Jr. St. N in St. Petersburg. [ Courtesy of the Flamingo ]

Nichols, who wasn’t an especially bookish guy, for decades didn’t think much of it, until people became especially interested in Kerouac’s history in St. Petersburg about a decade ago. Now the bar has a Kerouac mural on the outside wall and some Kerouac photos and novels on a wall inside.

RELATED: Glimpse inside the St. Petersburg home where Jack Kerouac lived

More recently, the Flamingo’s best-known patron might be former Navy SEAL and SEAL Team 6 member Kristin Beck, who became a public figure when she came out as a transgender woman in 2013. Beck, who gave Nichols a Navy SEAL plaque that hangs in the bar, was even interviewed inside the Flamingo for Lady Valor, the CNN documentary about her.

The evening before the anniversary party, Nichols said he expected a big crowd for the celebration because there would be 25-cent beer and hot dogs, served on square, buttered buns, like he remembers the ones at the St. Petersburg pier when he’d ride his bike there as a boy to watch people catch sharks.

Men shoot pool inside the Flamingo bar in St. Petersburg. [ Times (2011) ]

But, like most old bars in St. Petersburg, and everywhere else, it’s the regulars who show up on an ordinary night who keep the place going, and that night the place was full of them.

How regular? It also happened to be Nichols’ 76th birthday. Dawn Vasseva the bartender passed a card around the bar, and everyone seemed to have something personal to write in it.