David Letterman, who on Thursday finished an extraordinary 33-year run as a late-night host on US television, will long be remembered for his gap-toothed grin and rapid-fire wit by the fans who revered him.

But to me he’ll always be the man who got away from Rupert Murdoch.

• Late night legends: who’s the greatest talk show host of all time?
• TV king Letterman says farewell
• The interview that made John Oliver’s career

I became a Letterman fan 30 years ago in the mid-1980s when I moved to Los Angeles for work. Johnny Carson was the king of American talk show TV at the time but, as good as Carson was, for me he was just a warm-up act: Letterman came on at 12.30am when Carson was done and my wife and I rarely missed a minute of his nightly show.

Not since Graham Kennedy at his irreverent best had I seen anyone or anything like him. Letterman pushed boundaries, capable of going in unexpected directions – and to hell with the consequences.

I became such a fan of his that at my very first meeting with Murdoch over lunch in the 20th Century Fox commissary in late 1986, I gushed about Letterman’s abilities and, somewhat presumptuously, urged the all-conquering tycoon to grab him for his nascent Fox TV Network.

To my astonishment, Murdoch admitted he was already chasing him hard, but that Letterman was resisting his entreaties.

Rupert Murdoch attempted to poach Letterman for his Fox network. Photo: Getty

“But I’m going to keep on trying,” said Murdoch, who was aggressively trying to build Fox into a fourth force in American TV.

In the end, Murdoch failed to sign the comic. (Given Murdoch’s impatience with talent, that was probably a good thing for Letterman’s career longevity.)

Letterman stayed at NBC, hoping to succeed Carson whenever he retired. But when that eventually happened in 1992 he was passed over as host of the Tonight Show for Jay Leno. Letterman reacted by defecting to CBS.

The Late Show with David Letterman debuted on August 30, 1993. It bore a striking resemblance to Letterman’s previous NBC show, but for two things: he was much better dressed and so were his surrounds (CBS bought the famous Ed Sullivan Theatre on Broadway to seal the deal with him).

With Letterman’s signing by CBS and a move to an earlier head-to-head timeslot, a sometimes bitter rivalry with Leno was born. Letterman won the early rounds, but eventually Leno drew ahead in the ratings and stayed there.

This only proved to me that the lowest common denominator will invariably win in the end. Leno was a joke teller, while Letterman was a risk-taker. And I know who I preferred to watch.

This was lost on some critics this week, with one dubbing Letterman “TV’s biggest loser” because of his lack of ratings success against Leno. Fairfax outlets carried the assessment, appearing to endorse it, which was ironic: If we applied the same rule to newspaper sales, the Fairfax titles would be deemed vastly inferior to News Ltd titles because of their weaker circulation.

Jay Leno (pictured with Scarlett Johansson) was Letterman’s main competitor. Photo: Getty

Letterman’s retirement this week had me recalling a birthday present I was given in the late 80s when I returned to Australia. It was a slightly battered VHS video with several of his TV shows taped over the cassette’s original material by an American-based friend. I thought it was the coolest gift ever.

I played the video over and over for weeks, delighting in Letterman’s monologue, Top Ten list, stupid pet tricks, and the rest of the madness he brought to his show night after night in America’s early hours.

Years later, I still pulled that video out pretty regularly, marvelling at the comic’s wit, timing, even his interview skills. I must have laughed at some of his jokes a hundred times or more.

At some point along the way, I stopped watching Letterman regularly, even though the internet, cable TV, even local free-to-air programming made it easy to do so. (Come to think of it, maybe that’s why I lost interest.)

Letterman (right) with guest Bill Murray during the taping of the first Late Night with David Letterman episode in 1982. Photo: AAP

But, in the same way one might rush to the side of a dying relative we’ve neglected, I’ve been watching Letterman again as his retirement loomed. And I realised I’ll miss him terribly.

That’s because, as US critic Tom Shales recently observed, Letterman’s departure represents the end of the talk show era.

“What the networks have in those time slots now are really comedy-variety shows,” said Shales. “Letterman may have specialised in humour that was goofy, absurdist, deranged, but there was an underpinning of irreverent intelligence to it.”

All of which is reason enough to like him and to regret his retirement. The fact that he once said ‘no’ to Rupert Murdoch just makes me like him that little bit more.