“Come fly with me, let’s fly, let’s fly away”, sang Frank Sinatra, topping the charts in 1958. They did – his friends, aquaintances and lovers, that is. Dean Martin. Marlon Brando. Elvis Presley. Sammy Davis Jr. Michael Caine. Paul McCartney. Mia Farrow.

In 1965, Sinatra, who had previously owned a 40-seat airliner and a Morane-Saulnier MS.760 Paris – a French military trainer used as a business jet – took delivery of a brand new Learjet 23. This snappily designed six-seater, with its distinctive raked-back windscreen, stubby wings and pronounced wing-tip fuel tanks was truly something else.

For many, it was and remains the definitive business jet

Based partly on the design of a prototype Swiss fighter, its performance was sensational. It could fly as fast as a transatlantic Boeing 707. Up to 40,000ft, it could outclimb a US Air Force F-86 Sabre. Its twin General Electric turbojets were a civilian version of those thrusting the latest Northrop F-5 Freedom Fighter way past the sound barrier. The Learjet 23 was aerobatic, potent and glamorous. For many, it was and remains the definitive business jet.

Sinatra was certainly a big, ring-a-ding-ding businessman by 1964 when he signed the deal for his Learjet. Chairman of his own record label, director of his own film company, a major player in real estate and investor in a missile components manufacturer, he was flying very high indeed.

He wooed Mia Farrow with his 23, inviting her, after their first date in 1965 to a screening of None but the Brave (starring, guess who?), to his home in Palm Springs. “We were in LA”, Farrow recalled, “and I didn’t think I could do that – I didn’t have my pajamas or anything. He said, ‘Well, how I about I send my airplane for you tomorrow?” Farrow was on that plane with its snug, pressurised cabin trimmed in orange – just 4ft 11in (1.5m) wide and 4ft 4in (1.3m) high – complete with leather sofa and minibar. The following year, they flew on their honeymoon to the south of France in the Learjet, named Christina II after Sinatra’s younger daughter.

On 1 May 1967, Sinatra lent Elvis Presley his Learjet to elope from Palm Springs to Las Vegas with 21-year-old Priscilla Beaulieu. After an eight-minute ceremony at the Aladdin Hotel, they were back on the plane to Palm Springs. Their daughter, Lisa-Marie was born nine months to the day.

Sinatra flew Michael Caine on the jet to quiz him over the English actor’s intentions regarding his daughter, Nancy, whom Caine was dating. Dean Martin, one of Sinatra’s Rat Pack, was a regular passenger. The plane flew Sammy Davis Jr and Marlon Brando to Mississippi to join Martin Luther King Jr on a freedom march.

Although bought mostly by more conventional business tycoons than Frank Sinatra, the scintillating $495,000 jet made its name in Hollywood among those who would broadcast its qualities to the world. It was a prop in the popular ABC TV show The Dating Game (1965-73), flying contestants – among them budding starlets Farrah Fawcett and Lindsay Wagner and eligible bachelors Lee Majors and Arnold Schwarzenegger – to San Francisco or Las Vegas.

Danny Kaye bought a Learjet 23 and became a partner with the company. In the mid 1980s, a Learjet 23, piloted by the company’s salesman-pilot Clay Lacy, was used to film the breathtaking aerial sequences of Top Gun, starring Tom Cruise.

A personal touch

The Learjet, which had gone from design to production to cult status within a very short time, was the brainchild of Bill Lear, a self-taught inventor and high-school dropout born in Hannibal, Missouri in 1902. In the late 1920s Lear invented the Motorola for the Galvin Manufacturing Company. It was the world’s first successful car radio. He learned to fly, buying his first aircraft, a Canadian Fleet bi-plane trainer, in 1931 and developed early autopilot systems and radio direction finders for the aircraft industry. These, and other inventions, were to earn him more than $100 million during World War Two.

Lear also invented the 8-track cassette player

Lear also invented the 8-track cassette player, a pollution-free steam turbine engine for cars and buses (sadly, unsuccessful) and was forever dreaming up new ideas. He is best known, though, for the Learjet, a project he initiated when he was nearly 60.

In 1960, he founded the Swiss American Aviation Company at Altenrhein, Switzerland, working with the aircraft engineer Dr Hans-Luzius Studer and a team of Swiss, German and British engineers on the design of a business jet based on Studer’s FFA P-16, a prototype supersonic fighter jet. However, after prototype P-16s crashed, the Swiss Air Force bought British Hawker Hunters instead. Undeterred, Lear brought that project – his first aircraft was built in Switzerland – and a number of key ideas from Studer, back to the US. He would establish Learjet in 1963 in Wichita, Kansas – the home of Cessna and Beechcraft, two rival aircraft manufacturers. The man had a certain sense of humour, having named his daughter Shanda (as in Shanda Lear), and he quipped upon being handed an investment bond for $1.2m by the US government:  “Can you think of any place I can steal more engineers?”

That money went fast, but Lear was lucky. The crash of the first Learjet on a test flight in 1964, with a Federal Aviation Authority pilot at the controls, gave Lear the money he needed to push on with the project. The FAA pilot had forgotten to put the flaps down on take-off. The jet lifted to 10 or 20ft and then fell to earth. No one was injured, but the aircraft was written off, and Lear received an insurance pay-out of $500,000.

Undaunted

Crashes came to haunt the Learjet. It was a chic, lithe and very fast aircraft and designed to be easy to fly. But, in the world of early business jets, pilot error was rife: within three years of the first sales, 23 out of 104 Learjets crashed, four with fatal results.

Later series… are inherently safe

Improved pilot training and improved low-speed handling incorporated in the design of the Learjet 24 helped matters, but the 20-series Learjets were involved in too many accidents for anyone’s comfort. In January 1977 Frank Sinatra’s 82-year-old mother, Dolly, died when the Learjet 24 he had chartered to take her from Palm Springs to Las Vegas for an opening night at Caesar’s Palace flew into a blizzard and crashed on Mt San Gorgonio. Later series, including today’s bigger, quieter and far more efficient composite-bodied Learjets made by Bombardier are inherently safe.

Sinatra’s own Learjet 23 is currently under restoration. Much fuss was made over it on the occasion of the company’s 45th birthday in 2008 when the new, eight-seat Learjet 85 was announced.This latest aircraft is recognisably the successor to classic 23. “We pushed our designers to stay within that envelope”, said product manager Brian Nolan. Since then it was announced, a downturn in the market for business jets had kept the 85 project grounded. But up in the skies, 83-year-old Clay Lacy continues to wow air show crowds with aerobatic displays in his Learjet 23 as if it was still 1964 and Frank Sinatra was on the phone.

If you would like to comment on this story or anything else you have seen on BBC Culture, head over to our Facebook page or message us on Twitter.