The Gambler - on Wednesday, February 17, 7.30pm - is Tim's meticulously-researched touring show about the 10 greatest and most outlandish bets in 450 years of gambling history, which also entailed him racing a racehorse over 100 yards.
"It started for me when reading a book about very boring poetry," said Tim. "In the book was a footnote and I love footnotes. Basically, it told how the poet sailed 40 miles down the Thames in a boat made of paper. I thought, that's brilliant, and when I discovered it was the world's oldest existing maritime record, I thought: I can beat that and raise some money for Comic Relief. I still have a big soft spot for the paper boat bet because it was the one that kicked it all off for me," said Tim.
What followed was an attempt to row a bathtub across the English Channel. The French government wouldn't allow a rowing bathtub in their waters so he redesignated it as a boat, complete with a shower pole for a mast, and got himself a world record.
"I eventually got insurance against fire and theft, then I thought there must be more of these crazy bets that people don't know about.
"I started researching gentlemen's clubs, newspaper articles and all sorts of historical sources to find out more about them and try to make a list of crazy bets in history."
He did the paper boat bet himself in 2003 and came up with the show in 2011. Tim said: "The thing about it that's so important to me and to the audience, I think, is that the bets have to be historically valid and for me to be really honest about it all.
"They are real bets by real people with real results. Here were people who were so obsessed about winning something, either for the furthering of science or for fun or to make a load of cash. Inevitably there were a great many side issues that made a fascinating area for research. For example, Rothschild made bets that we would now see as insider trading."
Racing the horse? "It wasn't easy," said Tim, "because horses don't like racing against humans. They get a bit skittish. The race was held at Higham point-to-point racecourse in East Anglia but I'm saving the name of the horse for the show."
The order of the show is different every time, dictated by a member of the audience choosing a card. "Some people have bets on how many bets I win so I don't want to give too much away," said Tim.
"I wasn't particularly into research when I was younger. We talk about the Wellingtons, Nelsons and Napoleons but my mission is about the incredible and quirky people that history has tried to hide from us, like the baker who bet he could stand on one leg for 12 hours.
"My inspiration? It has to be 100 per cent Spike Milligan. I can't stop laughing at him. He was brilliant."
The Gambler follows on from Greenwich Theatre's sell-out talking head shows with Germaine Greer and David Starkey. "I think it's going to be a hilarious evening," said James Haddrell, Greenwich Theatre's Artistic and Executive director. "You can see it as a stand-up show but it's also a chance to hear someone who gets huge pleasure from historical research talking about these crazy historical bets. Tim's enthusiasm for these eccentric characters from history is infectious."
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