Before casinos changed the face and fortunes of Atlantic City, its most recognizable spokesman may have been a top-hatted, mustachioed tycoon known as Uncle Pennybags.

In the late 1920s, the jaunty character on the Monopoly game board, supposedly based on financier J.P. Morgan, literally brought the map of Atlantic City into millions of homes. Who didn’t long to visit the real Marvin Gardens, tread the famous Boardwalk, risk it all on a game of Chance? And make no mistake: games of chance were plentiful long before 1978.

Over the years, the city has embodied all that is wholesome (Miss America, Steel Pier) and everything mother warned you about (bootleg liquor, illegal gambling, houses of prostitution). Even Monopoly, a game beloved by generations of children, is at its heart a tribute to greed and the desire to run everybody else out of business.

Here is wild-and-woolly Atlantic City from the 1930s through the ’60s—four decades of prosperity and poverty, mayhem and hullabaloo.

1930s

During Prohibition, Atlantic City was an easy mark for smugglers, who surrepticiously guided boatloads of European whiskey through its maze of rivers and inlets. Known in short order for its gin joints and back-alley gambling dens, the city attracted a sinister element, including some of the most famous mobsters of the day.

In 1929, shortly after “Scarface” Al Capone ordered the St. Valentine’s Day Massacre, he met with fellow mobsters Lucky Luciano, Dutch Schultz and Meyer Lansky at the Ambassador Hotel, trying to broker a peace. When Lansky honeymooned here, he stayed in the penthouse of the Ritz-Carlton and was wined and dined by powerful political boss Enoch “Nucky” Johnson. Johnson, known for his involvement in rum-running and numbers rackets, was later jailed for tax evasion.

The Miss America pageant, pulled in 1927 because it was deemed immoral, was revived in 1933. To the delight and hilarity of all, the “talent” portion of the competition was introduced. On the Boardwalk, the big bands of the era held sway, wowing as many as 80,000 fans on a single summer day. It’s where bandleader Harry James introduced a skinny crooner named Frank Sinatra, and where Grace Kelly, whose family summered in Ocean City, went dancing. On the Steel Pier, the Diving Horse made a big splash.

1940s

After the 1941 attack on Pearl Harbor, Convention Hall became a makeshift military base for U.S. armed forces, training so many soldiers that it earned the nickname “Camp Boardwalk.”

The Claridge, Ritz-Carlton, Haddon Hall (known as England General Hospital) and others, served as training and rehab centers. Each day, recruits performed calisthenics on the beach, and each night the city went dark, with Boardwalk lights painted black so ships would not be visible to offshore U-boats. In November 1943, Atlantic City hosted a world peace conference, and within a year, the war in Europe had ended.

That same year a massive hurricane roared up the East Coast from Cape Hatteras; on September 14, 1944, it battered Absecon Island with winds that reached 85 mph. Area highways were submerged in up to five feet of water, and though two deaths were reported, the city survived largely intact, with damage to the Boardwalk minimal.

The 500 Club, a fixture in the city since 1918, reached its peak of popularity with performers like Dean Martin and Jerry Lewis (who first teamed up there), as well as Sinatra, Jimmy Durante and Sammy Davis Jr. Nighclub owner Paul “Skinny” D’Amato, a mob intimate, ran a race and sports betting parlor on the Northside that masqureraded as a cigar store..

1950s

During this decade, every major black entertainer of the time appeared at one of six nightclubs on Kentucky Avenue including Grace’s Little Belmont, the Paradise Club and Club Harlem. The star-studded lineup included Pearl Bailey, Cab Calloway, Sarah Vaughn, Redd Foxx, Nat “King” Cole, Moms Mabley, James Brown and Billy Eckstine.

But by the 1950s, automobiles and easy air travel had begun to erode Atlantic City’s popularity among tourists. Visitors who had once come by train and stayed for weeks spent a few days or hours before moving on. Florida and the Caribbean were the places to go; other Jersey Shore towns developed their own following and skimmed off even more of Atlantic City’s patron base. The city’s famous carnival atmosphere suddenly seemed tired and tacky; one newspaper even referred to AC as “Skid Row by the Sea.”

Soon poverty and crime took hold, and middle-class residents fled to the suburbs. The neighborhood known as the Inlet became particularly impoverished. It seemed that Atlantic City’s best days were behind her.

1960s

By the ’60s, many of the resort's great hotels had closed or been converted to cheap housing. Soon many would face demolition, including landmarks like the Breakers, the Chelsea, the Brighton, the Mayflower and the Marlborough Blenheim.

The 1964 Democratic Convention should have been a highlight of the decade. Instead, wrote historian David G. Schwartz, it was “a low ebb, revealing to the nation a city with decaying hotels, an inadequate infrastructure and few attractions.” The onetime “Queen of Resorts” had become an aging monarch.

But it still had its regulars. In 1967, the “Summer of Love,” 30 Sicilians and their bodyguards met Philadelphia mob boss Angelo Bruno for a confab at the 500 Club. Before long, the FBI began tapping the phones at “the Five” and monitoring the action from a parking lot across the street. It was the nadir of a once-great destination.

Then, less than a decade later, casino gambling was resoundingly approved by New Jersey voters and a year after that, Resorts International changed everything.

Today in this reviving city, the skyline is arcing ever higher, billions of dollars have been pledged for new development, and the future seems bright. And as visitors enter the city near the Expressway, they pass a plaque, erected by the city, in honor of Skinny D’Amato.

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