Originally published in the September 2015 Robb Report Private Aviation Sourcebook as “Come Fly with Me.”

At the start of the jet age, Bill Lear and other aircraft builders counted on celebrity endorsements—not just of their products but also of the lifestyle that went with owning a private jet. Frank Sinatra became an early adopter 50 years ago, in 1965, when he took delivery of one of the first examples of the Learjet 23. He named it Christina II, after his youngest daughter. A week after taking possession of the plane, Sinatra flew it to the Newport Jazz Festival, where he resurrected his singing career.

By modern standards, the Learjet 23 did not have a lot of space, just enough for two leather seats in back, a port-side seat near the door, a three- or four-person divan on the starboard side, and, on Sinatra’s plane, a pullout card table. His Learjet also included a liquor cabinet, the contents of which helped ease Sinatra’s fear of flying. (Before every flight, his valet—an ex-Navy officer—would call airports along the route to double-check weather reports.)

The jet’s real appeal to Sinatra and his Rat Pack friends was that it could shuttle them quickly between Los Angeles, Las Vegas, and Sinatra’s home in Palm Springs. With a top speed faster than 500 mph, the jet enabled hasty exits, which proved handy the time that Sinatra and Dean Martin got into fisticuffs with fellow diners at the Polo Lounge in Beverly Hills during a birthday celebration for Martin. When the plane picked them up at a nearby airport the following morning, Martin sported a black eye and blood on his shirt, while Sinatra wore a makeshift sling on his arm. No matter. They were up and away in a few minutes, heading to another state to wait out the news cycle and let their injuries heal out of the public eye.

Sinatra and Mia Farrow flew in the jet to the south of France for their honeymoon. He loaned it to Elvis Presley on the occasion of his elopement with Priscilla. Marlon Brando and Sammy Davis Jr. took it to Mississippi to join Martin Luther King Jr. in a civil-rights march, and Dean Martin loved to take it to movie sets. Sinatra sold the Learjet in 1967 and purchased a Gulfstream II.

Elvis was so impressed with jet travel that he bought two jets for himself. The first was a Corvair 880, a narrow-body airliner that he acquired 40 years ago, in 1975. He paid $250,000 for the plane and then spent more than $350,000 customizing the interior. When completed, it featured a forward lounge with club and divan seating, a conference room and dining area with its own refreshment center, a bedroom with a queen-size bed, and a private bathroom with a gilded washbasin and faucet. The jet’s videotape system linked with four television sets, and the audio system included 50 speakers. Like Sinatra, Elvis named the plane after his daughter, dubbing it Lisa Marie.

Shortly after buying the Corvair, he purchased a Lockheed Jetstar, for $900,000, to use while he waited for the work on Lisa Marie to be finished. The interior of that plane, called Hound Dog II, was far more conservative. It sat 10 passengers in a four-seat club area up front and a divan and two club seats in the rear.

Lisa Marie made its final passenger flight in August 1977, when the actor George Hamilton, Priscilla Presley, and the jet’s namesake flew from California to Memphis for Elvis’s funeral.