Just as it’s renowned for its casinos today, Atlantic City was once famous for its nightclubs. These were intimate, smoky lounges where visitors could see some of the day’s biggest stars, live and in person. Atlantic City had many legendary rooms, but the most famous was the 500 Club.

The “Five,” as it was popularly known, had humble beginnings. Phil Barr, a former trolley conductor and boxing promoter, moved to Atlantic City from Philadelphia in the mid-1930s, intent on opening a nightclub. In 1936, he bought and demolished two houses at 6 South Missouri Avenue, then built a two-story brick building. The nightclub occupied the ground floor, and above it Barr lived in a comfortable apartment.

The 500 Café, as it was initially known, was a small operation. During the day, a race-betting operation (illegal, naturally) attracted a stream of horse-lovers. At night singers and dancers graced its small stage. At the time, horse betting was rampant throughout the city, but there were not many full-fledged casinos. In 1941, Barr approached Paul “Skinny” D’Amato, the young part-owner of Luigi’s, the most popular illegal gambling den, with a proposition: bring his magic to the Five. Though D’Amato initially rebuffed Barr, they eventually agreed on terms and D’Amato opened up a major casino behind the Café.

After a gambling raid that sent Barr to prison, the Café closed for several months before D’Amato assembled a partnership to buy it. In May 1943, Skinny and his partners assumed control of the small club. Opening night was a fraught affair: D’Amato was so undercapitalized, he had to send his brother to a liquor store to buy bottles of liquor, a few at a time, barely balancing the cash register with his customers’ drink orders. But the new ownership was a success, and business was good.

In June 1946, D’Amato bought out one of the partners, and the venture was renamed the 500 Club, and that’s when the Five’s glory years began. Through his connections in the entertainment community, D’Amato brought the biggest stars of the day—from Liberace to Sammy Davis Jr.—to perform in his club. It’s impossible to estimate, but many people visited Atlantic City in these years just to see the acts at the 500 Club.

D’Amato did more than showcase existing performers: he launched new acts, most famously on July 26, 1946 when Dean Martin and Jerry Lewis first performed together on his stage. Martin and Lewis spent much of the next decade as one of the most popular attractions on radio and television, and starred together in 16 movies.

Martin and Lewis’ runaway success helped elevate D’Amato’s star as well. Even those who didn’t know much about Atlantic City learned that the 500 Club was one of the country’s top entertainment venues.

D’Amato’s biggest star, though, was Frank Sinatra. The two became friends in the late 1930s and though Sinatra’s career dimmed in the late 1940s, the nightclub owner maintained an unshakeable conviction in the singer’s talent. When Sinatra was at a professional and personal low point in the summer of 1951, D’Amato brought him in to sing at the 500 Club. The crowds overflowed into the street, proving Sinatra’s continuing appeal.

Later, when Sinatra’s career revived, he continued to perform at the 500 Club out of gratitude to D’Amato for his friendship. Each year, his August stints at the Five drew tens of thousands of visitors, despite the city’s waning popularity.

But Sinatra and D’Amato couldn’t hold off the wolves forever. Sinatra made his final 500 Club appearance in 1964, the same year that coverage of the Democratic National Convention revealed to the public just how dilapidated Atlantic City had become. The 500 Club continued, but part of the magic was gone.

What the city’s declining appeal couldn’t squelch was claimed by disaster. On June 10, 1973, a massive fire gutted the 500 Club, ending an Atlantic City institution. In many ways, it was the day the old Atlantic City died.

It would take another three years and the successful casino referendum for the resort to begin building for the future. Though Skinny D’Amato didn’t reap the bonanza of legal casino gaming, he was one of its boldest proponents. Without Skinny, it’s safe to say that Atlantic City’s post-war silver age would not have had the same luster. His 500 Club kept the resort afloat in tough times and pointed the way to the future.

By David Schwartz

David G. Schwartz (www.dieiscast.com), an Atlantic City native, is the Director of the Center for Gaming Research at UNLV and the author of several books, including Roll the Bones: The History of Gambling.