He has been shortlisted for the BP Portrait Award four times before, but last night Andrew Tift finally won it with a triptych depicting the former wife of his fellow artist Lucian Freud.
The work, entitled Kitty, is a portrait of Kitty Garman, the daughter of the sculptor Jacob Epstein. She was married to Freud from 1948 to 1953 and was painted by him many times, perhaps most famously in Girl with White Dog.
But undeterred by any comparison with Freud, a painter many believe to be Britain's greatest living artist, Tift, 38, produced a work praised for its intensity.
Sandy Nairne, director of the National Portrait Gallery, which organises the prize and exhibits the best of the submissions, said this year had brought an outstanding entry in the range and quality of portraits.
But Andrew Tift took first prize for a "remarkable and penetrating study". He was presented with the award by the singer Bryan Ferry in a ceremony at the gallery last night.
Inspired by the close-up and intense television interviews of John Freeman on Face To Face in the 1960s, Tift chose Garman as his subject because of her strong connections to Walsall, in the West Midlands, where he lives.
She used to live just outside the town and her mother, Kathleen Garman, an art collector, gave many works to the borough's art gallery.
Tift said: "I work in a highly detailed, intensely realistic manner and aim for an absolutely pure and objective likeness. I seek to convey people in the most understanding, intimate and sympathetic way that I can."
After having exhibited in the show 10 times and being shortlisted on four occasions, he had previously observed: "I do sometimes feel a bit like Tim Henman - nearly getting there."
The winner of the £6,000 second prize was Rafael Rodriguez Cruz, 29, from Mexico for Model 1, while Angela Reilly, 40, from Glasgow, took third prize with Self-Portrait. The annual £4,000 travel award was won by Toby Wiggins, who intends to journey in a camper van from Dorset to the New Forest and document the changes in agricultural communities.
BP has confirmed it is extending its sponsorship of the competition, which enjoys wide public support and some opprobrium from anti-oil industry activists. Des Violaris, the director of BP's UK arts and culture programmes, said: "The popularity of this competition with both young artists and the public who visit the National Portrait Gallery to see their work is testament to the vitality of portraiture in the UK. BP is extremely pleased to extend our involvement."
Currently in its 17th year of support, BP will extend its sponsorship deal from 2007 until 2011.
The exhibition of 56 portraits, picked from more than 1,100 submissions, runs until 17 September. Admission is free. It will tour to the Aberdeen Art Gallery and the Royal West of England Academy in Bristol.