The men behind the peephole just wanted to pay their way through school
During the country’s dry days, cousins Jack Kreindler and Charlie Berns started a speakeasy as a way to pay tuition for night school in 1922. Their very first speak, called the Red Head in Greenwich Village, served liquor in tea cups and in the building that now houses tapas spot Tertulia. They moved several times before making a permanent home at their current address in 1930. By that time, the duo had amassed quite the following.
“Everyone wanted to party with Jack and Charlie,” says Avery Fletcher, 21’s marketing manager and unofficial historian. “They built this phenomenal reputation and attracted artists, politicians, entrepreneurs and an entire ‘Who’s Who’ of the country.” What started as a means through night school became an entire career for the cousins. As a result, Jack never finished school, though Charlie did. “They were like two sides of a coin,” Fletcher adds. “Charlie was very studious and Jack fancied himself a cowboy. In fact, he would come to 21 in full cowboy regalia.” (His love of the Old West is the reason why the restaurant has its fabulous collection of Frederic Remington paintings and sculptures). It was the more conservative Charlie, however, who was issued a fine for $100 for violating Prohibition in 1929, before 21 opened. He eventually received a pardon from President Franklin D. Roosevelt.
The ingenious architecture ensured that multiple raids came up dry
Because of their “friendship” with local police, 21 operated under the federal radar — until Daily Mirror gossip columnist Walter Winchell was banned. In retaliation, Winchell printed a column that questioned why the club had never been raided. The Feds came knocking the very next day. Luckily for Jack and Charlie, something was awry with the search warrant, and they got away with a slap on the wrist. That incident, however, caused them to hire specialty architect Frank Buchanan to install a complex system to hide and destroy liquor, which included a “disappearing bar” that, with the flip of a lever, would dump shelves full of bottles into a chute that led to the sewer system. Buchanan’s work also included the clandestine wine cellar, hidden behind a 5,000-pound brick door that unlocked only when a meat skewer was inserted into a small hole at a particular angle.
The famous people (dead and alive) whose wine is still stored in the cellar
Though the disappearing bar no longer exists, the wine cellar does, holding more than 20,000 bottles, including the private stock of legends, living and deceased. The cellar still includes the stash of Frank Sinatra, Richard Nixon, Joan Crawford, Nelson Doubleday and many more boldface names. Today, it is now a coveted private room, hosting events for up to 22 diners. There’s also an antique table for two, just off to the side of the new banquet table. That table belonged to Mayor Jimmy Walker, who would dine alone in the cellar with his mistress. In 1931, Walker happened to be there when the restaurant was raided once again. Angry that he was trapped for five hours, he asked for a telephone (21 was the first restaurant to provide diners with phones), called the city police, and had them ticket and tow all of the federal vehicles. The Feds ended up finding neither booze nor their cars.
Notorious mobster Legs Diamond had a hit out on Jack and Charlie
Jack and Charlie preferred to keep their “connections” with the local police, instead of the mafia. This infuriated Albany mobster Jack “Legs” Diamond, who always wanted a piece of 21. “Diamond put the squeeze very hard on Jack and Charlie,” says Fletcher, “But they always avoided him somehow, and they were also paying off the police to make sure they had extra protection.” Diamond was fed up, and not only did he put a hit on Jack and Charlie, he decided to do it himself. As luck would have it, “The day before he was to carry it out, somebody took him out in Albany,” Fletcher explains.
What’s with the jockeys?
The first thing one notices when approaching the quaint townhouse: the 33 iron jockeys guarding the gated exterior. They were donated by famous stables throughout the country, attached to names such as Vanderbilt and Mellon, with the first gifted in the early 1930s. Believe it or not, even during NYC’s worst crime era, none of those very weighty jockeys have ever been stolen. Fletcher says that “there was one time when a guest climbed over the chain that keeps people off the stairs in front. She went over and up the stairs … and knocked them all over. She left a pile of jockey heads and jockey legs at the bottom of the stairs. It was quite the sight.”
The toy collection started as an ego contest
Look up: Hovering above the red-and-white checked tablecloths in the bar room is a ceiling decorated with dangling toys, including a model PT-109 boat from President John F. Kennedy; a baseball bat from Willie Mays; a pool cue from the set of The Hustler; and an Air Force One flyer from President Bill Clinton. The toy collection dates to the early 1930s. The first to appear was a model of a plane from British Airways, hung over the table in order to impress some investors. Turns out Howard Hughes happened to be in the dining room that day. “He said, ‘If you’re hanging his plane, you’re hanging my plane,'” Fletcher says. “So began a very elegant male ego contest.” Women eventually got in on the act, too: The ceiling holds ice skates from Dorothy Hamill and a tennis racquet from Chris Evert. The staff dutifully dusts each of the 1,000 pieces on a regular basis, treating each as if it were a priceless chandelier.
21 has a long history as a celeb haunt
There are nearly too many to catalog, but the restaurant’s website has a great diagram of celebrity tables in the bar room, from Dorothy Parker to Alec Baldwin to Alfred Hitchcock. Some favorite anecdotes: Bogie and Bacall had their first date at table 30, known as Bogie’s Corner. “We have a little plaque in Bogie’s Corner,” Fletcher says. “Miss Bacall still comes in to check that the plaque is still there.” Ernest Hemingway was known to raise some hell here. Legend has it that one night, he spotted a raven-haired beauty across the room and enticed her to the kitchen stairwell, where they had an … intimate encounter. Hemingway was horrified to learn the next day that the beauty was actually Legs Diamond’s girlfriend.
No matter how famous you are, there is still a dress code
21 was the last restaurant in NYC to drop the tie requirement for gentlemen, though jackets are still a must. At one point in time, however, women were not allowed to wear pants. Socialite Pat Buckley broke down that barrier when she came in for lunch one day. When told by the maitre d’ that pants were not permitted for women, she went into the ladies room, took off her trousers, and came back in just her un-tucked blouse and knickers, and said, “I’m ready to be seated for lunch now.” More recently, Michael Jordan came in to a private event without a jacket, which was allowed since the private rooms don’t have a code. After the event, however, Jordan went to have a drink at the back bar. Unable to find a jacket large enough to fit him, the staff had to ask him to leave.
New York’s first high-end burger was invented here
It was rare that a speakeasy served food, and the fact that 21 operated as a full-blown restaurant made it unique. Not many people know that in recent years, some of the country’s top chefs passed through 21’s kitchen, including Michael Lomonaco, Geoffrey Zakarian and Emeril Lagasse. Even fewer realize that 21 was the birthplace of the haute burger, a huge, Salisbury steak on a bun, meant to be eaten with a fork and knife. In 1950, when the burger was first introduced, it cost $2.75. In the 80s, the sought-after sandwich soared to $21. Today, it is $34. It’s customary to top it with the famous house 21 Sauce, a blend of tomato, mustard and seasonings, a mix originally created as a hangover remedy for a patron.
There are rumors of cocktails being invented at 21, but Fletcher points out that their histories are in dispute. “The Southside, for example, has a few different stories. One is that it was invented here, one that it was invented on the south side of Chicago, and one that it was invented at the Southside Country Club out on Long Island,” she says. “We’ve also been rumored to have created the Bloody Mary. But we’re leery to lay claim to it.”
21 has been on screen more than any other New York restaurant
It’s the most-filmed restaurant in NYC, making notable appearances in All About Eve, The Sweet Smell of Success, Wall Street, Manhattan Murder Mystery and many more. Recently, when the producers of the television show Blue Bloods came to shoot in the bar room, they determined star Tom Selleck was too tall for much of the low-hanging ceiling. They didn’t move ahead with the shoot, as they would have to take down too many toys.
Many bars and restaurants today celebrate the end of Prohibition; 21 does the opposite
After Prohibition ended on December 5, 1933, 21 threw huge parties, complete with pick axes, to allow patrons to help knock down the fake wall to unveil building No. 19, where much of the booze was stashed. Instead of continuing to celebrate Prohibition’s end, however, the restaurant prefers to celebrate its beginning. “If Prohibition hadn’t started, we might not be here today,” Fletcher explains. “We certainly wouldn’t have our exceptionally cool wine cellar and we wouldn’t have a lot of what ties us so much to New York and its history.”