When Stewart Lee made his first incursions into songwriting, by his own admission it was a limited success.

“I wrote about four songs, all in D,” he says. “I needed to learn more keys if I were to write more. I did try, but couldn’t do it – they started sounding like the ones I had already written! You have got to know your limitations.”

Brighton multi-instrumentalist Nick Pynn helped get his songs to the level where they could be performed in public – and he is the musician Lee is helping to celebrate this weekend alongside fellow Pynn collaborators Boothby Graffoe, Kate Daisy Grant, Georgia Seddon, Jane Bom-Bane and Mike Heron from Pynn’s favourite band The Incredible String Band.

“It’s like a benefit where no one has died,” says Lee. “Nick will get to see the sort of show that might be done about him if he were dead.”

Lee had met the Brighton-based musician while he was on tour with Boothby Graffoe in the early 2000s.

“I asked him if he would play fiddle and Appalachian mountain dulcimer which made the rhythmless s*** I did look classy.”

Some of those songs may well find a home in this weekend’s celebration of Pynn’s talents – including Russell Brand’s Wedding, Lee’s song about press hysteria.

“It’s very poignant now as back then Russell Brand was a rather lightweight trivial figure who had just married Katy Perry,” says Lee. “Now he’s an extremely serious political commentator who has got divorced from Katy Perry. It’s just unimaginable how much he has changed.

“I will probably do that and the half hour that hasn’t been on the telly up to that point from the series,” he adds, referring to Stewart Lee’s Comedy Vehicle, which is currently on BBC Two on Saturday evenings.

The rest of the Nick Pynn show was still being planned as Lee spoke to The Guide.

“It will end up as a fantastic comedy and music variety show that no one in their right mind would programme,” he says.

“I think we’re all going to play on a Mike Heron song at the end – but whatever I do it will have to be fairly simple!”

Making it up

Lee’s second Brighton show this week also focuses on music.

The Usurp Chance Tour combines two pieces of improvisation: The Conspirators Of Pleasure, combining prepared sitar and bass, electronics and Middle Eastern percussion, and John Cage’s Indeterminacy, featuring Lee as narrator.

While The Conspirators Of Pleasure is a collaboration between musicians Poulomi Desai, Al-Dinja, Seth Ayyaz and Simon Underwood, Indeterminacy sees Lee team up with long-time musical collaborator Steve Beresford and Tania Chen.

“Steve is another Zelig-like figure in music and comedy,” says Lee, referring to Woody Allen’s faux-documentary about a chameleon-like time-traveller blending into unusual situations.

“He was on the Vic Reeves album, has been a keyboard player for Prince Far-I and Ivor Cutler, the Scottish surrealist, and created music for The Day Today. He’s mainly a jazz guy, though he would call it improvisation.”

Lee is providing the “expression-less monotone voice” demanded by Cage to perform Indeterminacy, which sees him read a random selection from 90 one-minute-long short stories as Chen and Beresford independently improvise.

“They are supposed to improvise while not listening to what I’m doing,” says Lee. “There are lots of moments where what they are doing is supportive. It seems to be about how the ear makes sense of the information it is given – it can’t help but try to organise it and assume it has a deliberate relationship with the words, when this is not the case. You never know what is going to happen.”

Having performed the piece on and off over the past four years, Lee has deliberately tried to avoid preparing ahead of time to keep the experience as random as possible.

“Cage’s instructions are not to interpret it, or bring anything to it,” says Lee. “I have spent four years not finding out anything about John Cage – I didn’t want to be influenced by him. People try to tell you things about Cage – it’s a bit like the episode of The Likely Lads where they want to avoid hearing the result of a football match before they watch it on television, only the avant garde version.”

The stories themselves range from autobiographical tales from Cage’s own life to snatches of real life to morality stories from around the world. Although the time limit is still the same, the number of words in the stories change, requiring the narrator to change speed and tone rapidly between stories.

“There are a series of ten-second intervals on the cards telling you at which point you should be in the story,” says Lee. “You have to read them in the way they are intended, with the pauses, which work incredibly well. He really knew what he was doing. The juxtaposition can be funny or unexpected – the way the piece is made, it is never the same twice.

“You have to think on your feet. Some of the stories are not possible to tell in one minute. He has added an extra ten seconds on the end, so some don’t even work by his own rules! He’s created his own bit of chaos.

“We do from 30 to 60 stories from the 90. It doesn’t seem to matter; Cage doesn’t specify you have to do them all. We see how long people can stand it!”

Breaking through boredom

Through his comedy, Lee has followed one of John Cage’s maxims: If something is boring after two minutes, try it for four. If still boring, then eight. Then 16. Then 32. Eventually one discovers that it is not boring at all.

“I do find that, in comedy, the point at which something becomes boring is often the precursor to it being funny,” says Lee who, in his 2007 live tour (41st Best Stand-Up Ever), ran a Tom O’Connor adlib so far into the ground it became hilarious.

He leaves some space for improvisation in his comedy but, unlike the musicians he is working with, Lee finds he has to go back to his initial story or point.

“You hear it in 1950s and 1960s modal jazz like Sonny Rollins or John Coltrane,” says Lee. “With Coltrane’s My Favourite Things he starts with the tune, goes off for half an hour then comes back to the same tune again.

“For me, improvisation has to be a little like that: you have to go back to where you started.”

  • Stewart Lee And Friends: Celebrating The Music Of Nick Pynn is at Brighton Dome Concert Hall, Church Street, on Sunday, May 23. Starts 7.30pm, tickets £16, call 01273 709709
  • The Usurp Chance Tour is at Komedia, Gardner Street, Brighton, on Tuesday, May 25. Starts 8pm, tickets £10, call 0845 2938480.