Stars in the Sky
Sinatra used his Learjet to transport his famous Rat Pack and other showbiz friends to movie locales and wild times in Las Vegas.

Stars in the Sky

In today’s world, it’s less unusual for a top celebrity to own a jet than to fly commercially. That was far from the case only a few decades ago, however. Here’s a look at some of the luminaries who pioneered the use of private aviation.

Frank Sinatra

In 1957, composer Jimmy Van Heusen and lyricist Sammy Cahn wrote “Come Fly with Me” for Frank Sinatra. The song not only became a standard for the so-called Chairman of the Board, it also became an anthem for the first generation to enjoy the private jet age and the freedom it afforded to travel luxuriously, spontaneously and rapidly.

Not surprisingly, Sinatra was one of the first Learjet owners. From 1965 to 1967, his Learjet 23, tail number N175FS, racked up 1,500 hours transporting him, his famous Rat Pack and a host of other showbiz friends, including Elvis, to movie locales, wild times in Las Vegas and the sanctuary of Palm Springs, California.

The Lear was not Sinatra’s first airplane, nor would it be his last; he later upgraded to a Gulfstream II. But the Learjet was his most notorious aircraft. This was the airplane the then 51-year-old Sinatra used to squire actress Mia Farrow on their globetrotting, whirlwind romance. It doubled as the designated escape vehicle to get out of town fast after a night of overindulgence and fisticuffs.

This was also the airplane that took Sinatra to Vegas when he debuted his award-winning A Man and His Music big-band show with the Count Basie Orchestra in the Copacabana Room at the Sands Hotel in 1966. Of course, the opening song was “Come Fly with Me.” By 1966, that was, after all, how most visitors were coming to Las Vegas.

Other celebrities and business leaders took note of Sinatra’s latest mode of travel and it wasn’t long before “Come Fly with Me” was sung by a chorus.

Bob Hope

For more than three decades, Americans were used to seeing Bob Hope TV specials that showed him stepping out of an Air Force cargo airplane to entertain troops at war. Stateside, his ride was decidedly more plush. In 1967, he bought a 10-passenger Lockheed JetStar, tail number N18BH.

The four-engine jet began as a military project during the 1950s and was later immortalized in the 1964 James Bond movie Goldfinger. It climbed at a brisk 4,150 feet per minute and had transcontinental range. The Air Force bought a fleet of them, which it designated VC-140Bs. At one time or another, they flew every U.S. president from Johnson to Reagan. One is on display at the LBJ Museum in Austin, Texas.

Other luminaries were also attracted to the model. Howard Hughes would escape seclusion to take the controls of his, and Elvis christened his Hound Dog One. The aircraft’s original engines slurped a prodigious amount of fuel and were notorious for their high-pitched noise, so Lockheed began offering a retrofit with Honeywell TFE731 turbofan engines in 1976. Bob Hope was one of the first customers for the conversion. He kept his JetStar until he died in 2003, at age 100. His estate sold it. In 2010 it turned up on the market with an asking price of $400,000. In 2011 it was removed from the FAA registry.

Hugh Hefner

The so-called “sexual revolution” was a dominant cultural theme during the 1960s, and arguably no one benefited more from it than Playboy founder Hugh Hefner, who used some of the profits from his magazine publishing empire to begin flying privately.

On a 1966 commercial flight to London, he came up with the idea of having his own airplane, Big Bunny. It was a 1968 McDonnell Douglas DC-9-32 airliner, tail number N950PB, painted all black, emblazoned with the Playboy bunny logo on the tail and outfitted as a flying pleasure palace. “Hare Force One” featured a guest bar/lounge, a disco and a private stateroom with a huge six- by eight-foot elliptical bed covered in exotic furs. Hefner, who had begun his career as a cartoonist, dictated much of the design. He used the aircraft for international jaunts, commuting between his corporate offices in Chicago and the Playboy Mansion in Los Angeles, and squiring a long list of lovelies.

Although the focus was clearly on fun, the aircraft was professionally crewed and managed. Continental Airlines trained the leather-clad “jet bunnies” who served as stewardesses. Initially, the well-regarded flight department at Purdue University provided pilots and managed and maintained the aircraft as part of its “airlines program.”

Hefner’s empire hit a rough financial patch in the mid-1970s and he was forced to sell Big Bunny in 1976. The airplane was repainted, stripped of its hedonistic interior and pressed into airline service in Venezuela and Mexico. Much of the airplane was scrapped in 2008.

Malcolm Forbes

Malcolm Forbes was another ­publishing magnate who understood the power of branding. His Boeing 727, the Capitalist Tool, was painted in bold shades of green and gold and flown relentlessly to promote Forbes magazine. Compared with Hefner’s ride, Forbes’s was button-down corporate, even staid: the cabin featured a monochromatic grand lounge with multiple conversation groupings of leather executive single seats and divans with cocktail and card tables.

It wasn’t so much what was on Forbes’s airplane as who: Hollywood’s A-list, including Elizabeth Taylor; the politically powerful, such as former secretary of state Henry Kissinger, defense secretary Caspar Weinberger and numerous governors; legendary CBS News anchorman Walter Cronkite; and various captains of industry. Forbes collected the rich and powerful much like he collected his famous Fabergé eggs. The jet, like his mega-yacht the Highlander, was a vehicle he used to bring them all together. He employed it for exotic outings to his Moroccan palace, his French chateau and his private Fijian island as well as for his global hot-air-balloon and motorcycle adventures.

Elvis Presley

Elvis Presley caught the private jet bug from Sinatra and later purchased a pair of JetStars. However, with his film career behind him in the 1970s, he focused increasingly on concert tours and needed a larger airplane. In 1975, he acquired a quad-jet Convair 880 from Delta Airlines. The model resembled a Boeing 707, except that it was slightly smaller and faster. Smarting from the 1973 Arab oil embargo, the airlines were eager to unload them, and Elvis snapped his up for less than $1 million. He ripped out the airline-style interior and had it customized with executive seating for 29, a private bedroom and bathroom with gilded faucets, a conference room and what was then a state-of-the-art entertainment system. Elvis named the airplane Lisa Marie after his daughter.

In 1977, the then 42-year-old Presley was hours away from boarding the Convair when he was found dead in his Graceland home in Memphis, Tennessee. The airplane was subsequently sold, but his estate reacquired it in 1984 and moved it to the Elvis Presley museum at Graceland. It remains one of the museum’s most popular exhibits.

Paul Newman

Despite being one of the U.S. movie industry’s most bankable stars during the 1960s, Presley was never really comfortable with the Hollywood scene. Neither was actor Paul Newman, who captivated film audiences in critically acclaimed films such as The Hustler, Hud, Cool Hand Luke and Butch Cassidy and the Sundance Kid.

Newman spent his free time racing cars and raising his family quietly in Connecticut with his wife, actress Joanne Woodward, whom he married in 1958. He bought his jet largely to support his car racing. On any given weekend you could find him behind the wheel at a Sports Car Club of America race or in the pits cheering on the IndyCar drivers of his Newman-Haas race team. And on the ramp at a nearby airport sat N499NH, his electric blue 1981 Sabreliner 65. Woodward sold the airplane after Newman’s death in 2008, but it is still flying today from its new base in Alabama.

Adam Khashoggi

One of the largest private jets in the 1980s belonged to celebrity Saudi arms dealer and international fixer Adnan Khashoggi. From the 1960s to the late 1980s, wherever there was a flashpoint in the world, from Yemen to Nicaragua, Khashoggi was not far behind. Between 1970 and 1975, Lockheed reportedly paid him more than $100 million in sales commissions. In 1982, his Triad Holdings company purchased a stretch DC-8 four-engine jetliner and had a California company install a luxurious sculpted interior, complete with a star-map ceiling. The airplane’s dishes alone reportedly cost three-quarters of a million dollars. The DC-8 was fitted with a large lounge and three private staterooms.

Although Khashoggi was in a profession that demanded discretion, he seemed to crave the media spotlight, often hosting elaborate parties on the airplane with Hollywood celebrities and international dignitaries and inviting coverage of his lavish lifestyle. This in-your-face visibility helped make Khashoggi a prime target of international law enforcement, and his finances subsequently unraveled. The airplane was sold in 1986. Two years later, Khashoggi was arrested in Switzerland and extradited to the U.S., where he stood trial and was acquitted on fraud charges. He now reportedly lives a somewhat more modest life in Monaco.

Prince Bandar

Large as Khashoggi’s airplane was, another U.S.-based Saudi had an even larger one. Prince Bandar, who served as his country’s American ambassador, parked his Airbus A340 jumbo jet at Washington, D.C.’s Dulles Airport during his tenure from 1983 to 2005. Often on weekends he used it to commute to his 56,000-square-foot, $135 million ski lodge in Colorado, where he entertained guests. Bandar was a fixture in the diplomatic corps and its leading bon vivant. He was such a frequent White House visitor that the Bush family began referring to him as “Bandar Bush.”

Bandar’s jet became the focal point of an arms bribery scandal in Great Britain shortly before he left Washington. Britain’s Serious Fraud Office uncovered $240 million in payments from British Aerospace to the Saudi Embassy in Washington over the course of a decade that were allegedly used to defray the A340’s operating expenses after Bandar allegedly helped steer an $80 billion Saudi arms buy the company’s way. The investigation was dropped in 2006 and Bandar was never charged.