Tim Vine, winner of the Funniest Joke of the Fringe award: 'making a quip as funny as possible is an art'

Tim Vine has won the funniest joke award at the Edinburgh Festival 2014 (PA)

Writing one-liners is a serious business.

They sound offhand, casual, 10 seconds of hilarity, but behind them lie hours of tinkering with unfunny things such as word order and commas. Take Tim Vine, who won Dave’s Funniest Joke of the Fringe award this week, for the second time. In the award’s seven-year history, 2009 is the only year he failed to be nominated, when he did not appear at the Fringe. His 2014 winner is typical: “I decided to sell my Hoover… Well, it was just collecting dust.”

“It’s not necessarily my favourite joke in the show,” he says in Edinburgh, on his way to the first of two shows of the day. If that sounds nonchalant, bear in mind that his hour contains somewhere close to 200 one-liners. Some are borne of idle conversation, others from intensive sessions where he locks himself in a library and writes all day long.

“People assume that I think about nothing else but jokes. Most of the time, I’m thinking about other things, but I do have a notebook,” he says. More often than not, he works backwards, writing from punchline to set-up. “I hear punchlines in everyday conversation and think, ‘How could we get there in a different way?’ If someone says, ‘Serves him right,’ I’ll think, ‘Right, OK… A friend of mine’s got a left arm missing. Serve him right.’”

When it comes to wordplay, it’s a case of the simpler, the better. Ria Lina was a runner-up for her succinct gag: “I wanted to do a show about feminism, but my husband wouldn’t let me.” She prefers another of her one-liners – “If a pathological liar gets raped by a wolf, then set on fire, what should they cry?” – but edgy is a quality that comes low on the list when it comes to ranking puns. What makes a winner? “Jokes are a bit like electrons,” she says. “If you stare directly at them, you can’t see them, they dart off. You think, ‘There’s something in that…’ and then you let it brew.”

Lina is, incidentally, furious that Dave has published her joke with a full stop instead of a comma between phrases, but these are the obsessive fine-tunings that make comedy gold. “The process of writing a one-liner is very quick but the process of perfecting it is not,” says Bec Hill, another runner-up. “When you’re wording a joke, if it’s not grammar- or word-perfect it can completely change its impact.” Hill started out writing one-liners on Twitter. When they got a good reaction, she set up Pun Run, which takes place every two months in London, and filtered choice one-liners into her act, including: “I was given some sudoku toilet paper. It didn’t work. You could only fill it in with No 1s and No 2s.”

Once honed on paper, one-liners need to be road-tested on an audience. “I know it sounds daft, but sometimes you think to yourself, ‘Which way round shall I put it?’” Vine says. “‘I’ve got a friend who’s a tent peg. He’s driven himself into the ground.’ It doesn’t really get much. But you could do, ‘I’ve got a friend who’s driven himself into the ground. He’s a tent peg.’ It may never get beyond a weak laugh and I’ll drop it. Or I’ll tell it and shout, ‘Come on!’ after it.”

In other words, however much one-liners rely on good writing, how you tell ’em still counts. And there is a fine line between guffaw and groan. Vine’s joke “I’d like to start with the chimney jokes – I’ve got a stack of them. The first one is on the house” also made it on to the 10 Worst list this year. “I used to introduce my puns by saying, ‘Here are some of the worst jokes I’ve ever written,’” Hill says. “And they got groans because people were expecting bad jokes. As soon as I stopped leading in with that, I got laughs. They’re exactly the same jokes.”

After all the hard work that goes into crafting the perfect one-liner, there is always the risk that it might become too well-loved. For Vine, this latest award just means more work. “It kills the joke. Whichever joke wins, it’s cursed. I’ll do it today and it will probably get a cheer rather than a laugh. But, ultimately, I’ll have to drop it.”