Fourteen years after he first submitted a painting for the award, Walsall's Andrew Tift has finally won the accolade of being the UK's top portrait artist.
Tift's work, Kitty, a triptych of Lucian Freud's first wife, was selected from a record 1,113 entries for the BP Portrait Award, now in its 27th year.
This year was the fourth occasion that the 37 year-old Tift was short-listed.
His subject, Kitty Garman, was painted by Freud several times, most famously in Girl with a White Dog (1950-51) at Tate Britain, as well as Girl with Roses.
The pair married in 1948 but broke up after four years when Freud embarked on an affair with society beauty Lady Caroline Blackwood.
Tift, whose previous subjects include Tony Benn and a painting of Neil and Glenys Kinnock, which hangs in the National Portrait Gallery's permanent collection, has exhibited in the BP Portrait Award ten times.
The style of his monochrome portrait of Garman, the daughter of the sculptor Sir Jacob Epstein, was inspired by the TV series Face to Face, broadcast between 1959 and 1962.
The painter wins #25,000 and a #4,000 commission for his work, painted with acrylics on board.
He was presented with his award by singer and art collector Bryan Ferry at the National Portrait Gallery.
The artist said: "I saw Freud's painting of Kitty at the New Art Gallery in Walsall and thought I would like to do an almost identical image 60 years later.
"The last image on the right of my triptych is meant to directly echo the Freud pose.
"I visited her in her little village in Cambridge for a day a nd took almost 400 photographs.
"I chose to paint it in black and white because I was inspired by the programme Face to Face, where the camera work on the guests was almost like a visual interrogation.
"I wanted to present it like a conversation. I wanted to capture the different expressions in her face as she was absorbing thoughts and formulating sentences while we were talking. We talked about Lucian Freud a lot.
"She's 79 and very frail and her home help was there, running around and knocking over my tripod and things as I was taking photographs."
He added: "Winning is amazing. It's almost like my whole career has been centred on doing this every year.
"I've been submitting work to the Award for 14 years. I've got around 100 ideas at the moment and will spend my money developing them and maybe buying some CDs from Amazon.
"But it will be strange because once you have won you can't enter the prize again."
Rafael Rodriguez Cruz, aged 29, from Mexico, took second place for Model 1, from Models of a Self Portrait, while third prize went to Glasgow-based Angela Reilly, aged 39, who worked as an illustrator before painting full-time, for another self portrait.
National Portrait Gallery Director and chair of the judges Sandy Nairne said: "This year's BP Award brought an outstanding entry in the range and quality of portraits.
"We have a very strong shortlist of prizewinners and Andrew Tift's first prize winning entry is a remarkable and penetrating study."
It was also announced that BP is extending its sponsorship of the competition to 2011.
The winner of the #4,000 BP Travel Award was Toby Wiggins who will travel in a van from Dorset to the New Forest to document the changes in agricultural communities.