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Rat Pack stalwarts Dean Martin and Frank Sinatra lent Lear's private jet an invaluable aura of cool during the mid-1960s. [John Bryson/Sygma/Corbis]
Rat Pack stalwarts Dean Martin and Frank Sinatra lent Lear’s private jet an invaluable aura of cool during the mid-1960s. [John Bryson/Sygma/Corbis]
It wasn’t until the age of 50 that Frank Sinatra owned his first Learjet, but for the next two years it would become perhaps the most notorious mode of transportation for Rat Pack members and their friends. It was the ultimate in cool, and for designer Bill Lear, exactly the kind of marketing he wanted for his pet project.

Now celebrating its own 50 years, the Learjet was not the first private jet on the market, but it was by far the fastest. Given its list of high-profile clients—not to mention one-time VP of public relations Danny Kaye (the actor, comedian and pilot)—it quickly became an icon. It dominated the private jet market from its inception in the early 1960s through Bill Lear’s sale of the business to Gates Rubber Company in 1967, until around 1977. After some rocky years, Bombardier Inc. took over in 1990, and continues to roll out aggressive new models, with the latest and largest of the bunch, the Model 85, set for release this year.

By the time Bill Lear was conducting flight tests of the famed bizjet, at the age of 61, he was already successful. He is credited with more than 200 patents, and his inventions included the car radio, the 8-track tape, an aircraft autopilot and automatic landing system, among others.