David Fisher's striking likeness of Frome painter and personality Philip Ledbury was chosen as the winner of the Holburne Museum in Bath's 2008 Portrait Prize by a panel of expert judges.
Entitled Dead Man Posing, it captures Mr Ledbury, who was diagnosed with leukaemia in 2004 and given a maximum of five years to live, relaxing and smiling with a cigarette and a cup of tea.
Along with the title, Mr Fisher, from Midsomer Norton, has won a £5,000 commission to paint a portrait for the Holburne's collection.
The museum's only requirement is that the subject should play an active role in the cultural life of the region.
Previous winners have painted the jazz saxophonist Andy Sheppard, Glastonbury Festival organiser Michael Eavis, and the three directors of Aardman Animations, Peter Lord, David Sproxton and Nick Park.
The judges were unanimous in selecting Mr Fisher's painting as the winner.
Humphrey Ocean, Victoria Glendinning and John Leighton agreed the portrait succeeded in convincing people that the subject - or sitter - was someone with whom they had a personal connection.
A delighted Mr Fisher said: "My most successful paintings have been when the subject has inspired me and I have felt passionate about them.
"None more so than Dead Man Posing. Philip Ledbury has only recently come into my life through art, a man diagnosed three years ago with leukaemia. His passion for life is inspiring.
"His desire to live life to the full – 'quality not quantity' is a favourite saying of his – plus the wicked sense of humour he has, were enough to create the urge to paint his portrait and, I hope, in turn, make a fitting record of the man."
Since his diagnosis, Mr Ledbury, 58, has refused to let leukaemia beat him and says the disease has helped reveal a whole new side of his personality and a new career that he never even knew existed.
He has published his autobiography Dead Man Writing and successfully exhibited a series of paintings he created some years ago.
At a ceremony at which Mr Fisher was announced as winner, Mr Ledbury wore the same suit, shirt and tie and held the same mug as he does in the painting.
Museum director Xa Sturgis said: "I am very happy that the panel chose David Fisher's portrait as the winner of the Holburne Portrait prize.
"It has a wonderfully strong and warm presence and gives one a real sense of knowing the person it depicts.
"It was an even greater pleasure to meet Mr Ledbury on the evening of the prize-giving (complete with shirt, tie and mug) and to be in the presence of the painting made flesh.
"We look forward to working with David on his commission for the Holburne's collection."
In addition to the prize commission, two other popular winners were announced. There was to be one People's Choice award, voted for online on The Bath Chronicle's website www.thisisbath.co.uk, and on paper at the Chapel Row Gallery where the shortlisted entries were on show.
But the organisers decided to award two distinct prizes after it became clear online voters wanted one winner and the gallery visitors another.
The online winner of the People's Choice online vote was former GP Katy Sullivan for her portrait Calm. And the paper People's Choice winner was Sue Burns for her portrait of her son, Joe.
The paintings are on display until Tuesday, October 28, at Chapel Row Gallery, as the Holburne is currently undergoing a major refurbishment. The exhibition is supported by the Friends of the Holburne Museum, Chapel Row Gallery and Bath Royal Literary and Scientific Institution.