Tony Bennett performing at Playboy’s Lake Geneva resort, Wisconsin, late 60s. Courtesy of Playboy.
I talk about the basic nuts-and-bolts day-to-day operation of the Playboy clubs. These were small-ish venues laid in a well-managed circuit across the country (and, eventually, the world), each encompassing several rooms within. By comparison, the more traditional nightclubs, like the Persian Room, the Latin Quarter, or the Copacabana were gigantic venues with gigantic cover charges. The Playboy rooms were more in the spirit of the Village Vanguard or the Blue Angel, and priced within the range of the average Joe. The key word that everyone uses to describe the Playboy club – that is to say, all the rooms in all the clubs – is “intimate.” Hugh Hefner wanted to put the Playboy lifestyle within the reach of every man, and he knew he wouldn’t achieve that goal if he priced himself out of the game. From the beginning, the clubs were a destination for men who had more taste than they did money.
Another phrase that everyone uses in reference to the Playboy circuit is “up and coming talent”; today, the buzz word would be “emerging artists.” The mathematics of the situation – the size of the rooms and the reasonable cover charge – dictated that Playboy couldn’t outbid the Copa for superstar headliners like Nat King Cole, Frank Sinatra, or Judy Garland. Playboy was a place, were new talent was discovered, nurtured, and eventually sent on its way to bigger and better-paying venues. As is well known, for instance, Playboy hired both Aretha Franklin and Barbra Streisand before anyone had heard of them. It wasn’t until later, when the company opened its large-scale resorts, like Lake George, that Playboy had Vegas-style showrooms and paid Vegas-level fees to the talent, that they were able to attract iconic names like Bob Hope and Sammy Davis, Jr…
The major exception was Tony Bennett: he was probably the single biggest name ever to work the Playboy clubs, and probably the only Playboy regular who came to the club circuit at the height of a career that already included a ten year-run of hit singles. He was already a huge headliner by 1960, when the first club opened in Chicago, and his star rose even further when, at the zenith of the Playboy era in 1962, Tony landed the single biggest hit of his life – one of the biggest-selling records of the era, “I Left My Heart in San Francisco.” This turned out to be the beginning of a new lucky streak of successful singles that continued with “I Wanna Be Around,” “The Good Life,” “Watch What Happens” and “If I Ruled the World.” More than any other Playboy artist, Tony was continually on the charts throughout the 1960s.
Tony worked at the Playboy clubs not because, unlike most of the artists around him, he needed the break: he worked there because of his friendship with and admiration for Hugh Hefner. Tony understood the Playboy ethos because he had a part of it from the very beginning: he knew that Playboy’s mission statement wasn’t just about sex, or even just about music: the operative word was “fun.” It was a kind of fun that involved attractive people, good music, informed conversation, and a healthy dose humor. Playboy was creating a sophisticated, dressed-up party scene for adults; the kids had their rock-and-roll dance parties and sock-hops, the older folks had The Lawrence Welk Show, this was something for the 20 and 30 year olds. That party was the basic content, and the packaging or delivery system was an ever-evolving sequence of different media: first the magazine, then a music festival, then television, and then a series of clubs that blanketed the globe.
Later on, Bob Dylan famously described the composers who were based in the Brill Building as having songwriting “down to a science.” The same thing can be said for Hef: he had party-making down to a science.
Tony and Hef were both born in 1926 and both served their country during the Second World War; they met in Chicago in 1956, at a point when Tony already had landed his first hits and Hefner’s magazine was barely two years old. Tony loves to tell the story of how he first broke though in Chicago thanks to another one of that city’s favorite sons, the legendary Nat King Cole. In the early 1950s, Tony enjoyed a hugely successful run on the charts with hit singles like “Because of You,” “Cold, Cold Heart,” “Blue Velvet,” “Rags to Riches,” etc, led to a string of successful engagements around his native New York. “I was very big in New York City – everybody knew me. I played Ben Maksic’s Town and Country in Brooklyn; I used to fill the place up for two-week engagements four times a year. But nobody knew me outside of the east coast. Not in Chicago, the Midwest or Los Angeles.”
Then, through an unusual series of events, Tony recalled, he was asked at the last minute to fill in for Nat Cole at the Chez Paree in Chicago. “President Eisenhower invited Nat to come to Washington and sing for him at the White House.” This was the White House Correspondents Dinner on May 24, 1956, which interrupted Cole’s run at the Chez Paree. “So Nat said, ‘Tell them to get Tony!’ That’s how he broke me into Chicago. Because I took Nat’s place that night, I went over real big at the Chez Paree, and then they booked me regularly after that.”
Tony took to Chicago like it was his second home town; he particularly liked hanging out at the Black Orchid in the Near Northside area, which was owned and operated by Paul David “Pauly” Raffles. “That’s where I met Hef,” Tony said. “Those were great days, those Chicago days. The Black Orchid had great comics, like Larry Storch and Jack E. Leonard, and Pauly invented the piano bar in the lounge. He had girls in scanty clothes, and a little showroom in the Black Orchid. It was the hippest place to go to. You’d see a great show with a comic and a singer, and then they’d always have a great piano player, like an Ace Harris, then we’d all go over to Pauly’s apartment at like two AM, and stay there until seven in the morning, and just have big jam sessions.
“There also was another spot we liked, the Key Club, which was in the back of the Chez Paree, where Erroll Garner would come over there and play after all the public left, it was just the chorus girls, Lenny Bruce, Hef, and all of us guys. Hugh was in the middle of all this.” As Tony puts it, “He was a very introverted, quiet guy. His genius was that he saw all this fun that everybody was having, and he figured out a way to incorporate it. That’s how those Playboy Clubs came about—which was ingenious! He was a bright enough businessman. He just said, ‘Take something where everybody’s having fun and make it a product. Make it work.’ And it worked, boy! It worked into millions and millions of dollars.”
To be continued,
First of a series
You can read more stories in my books Playboy Swings and The Persian Room Presents