Vettriano left school at 16 and later became an apprentice mining engineer. For a short time in the late 1960s, he had a summer job as a bingo caller at the Beachcomber Amusements on Leven Promenade. Vettriano took up painting as a hobby in the 1970s, when a girlfriend bought him a set of watercolours for his 21st birthday. His earliest paintings, under his birth name “Jack Hoggan”, were copies or pastiches of impressionist paintings; his first painting was a copy of Claude Monet’s Poppy Fields. Much of his influence came from studying paintings at the Kirkcaldy Museum and Art Gallery. In 1984, Vettriano first submitted his work to the Shell-sponsored art exhibition in the museum.

In 1987, when he was 36, Vettriano left his wife Gail, seeking to emulate Paul Gauguin. He quit his job in educational research, and moved to Edinburgh, where he adopted his mother’s maiden name. He applied to study Fine Art at the University of Edinburgh, but his portfolio was rejected.

In 1988 Vettriano submitted two canvases for the Royal Scottish Academy annual show. Both paintings sold on the first day and Vettriano was approached by several galleries. Further exhibitions followed in Edinburgh, London, Hong Kong and Johannesburg. In November 1999, Vettriano’s work was shown for the first time in New York City, when 21 paintings were displayed at The International 20th Century Arts Fair at The Armory. More than 40 collectors from the UK flew out for the event and 20 paintings were sold on the opening night.

In 1996 Sir Terence Conran commissioned Vettriano to create a series of paintings for his new Bluebird Gastrodome in London. The seven paintings, inspired by the life of Sir Malcolm Campbell, hung there for ten years. Heartbreak Publishing, Vettriano’s own publishing company, produced a boxed set featuring signed, limited-edition prints of all seven paintings to mark the 75th anniversary of Sir Malcolm Campbell’s final World Land Speed Record. The Bluebird paintings were auctioned by Sotheby’s at the Gleneagles Hotel in Perthshire on 30 August 2007, and made more than £1m in all: the most expensive was Bluebird at Bonneville, bought for £468,000.

Vettriano has donated several works of art to be sold in aid of charities, including the Terrence Higgins Trust. In September 2001, Vettriano donated a painting, Beautiful Dreamer to a charity auction, which was held at Sotheby’s in aid of Help the Hospices. In 2008, a drawing he made of that subject sold at a charity auction in aid of the Oriel Plas Glyn-y-Weddw Gallery in Llanbedrog, North Wales in July, helping to keep the gallery open.

His easel paintings cost between £48,000 and £195,000 new. According to The Guardian he earns £500,000 a year in print royalties. Vettriano’s 1992 painting, The Singing Butler, has been the best-selling image in Britain. On 21 April 2004 the original canvas of The Singing Butler sold at auction for £744,500. It had been rejected in 1992 by the Royal Academy summer exhibition. The composition for the painting, as discovered by Scottish designer Sandy Robb, had been sourced from the Illustrator’s Figure Reference Manual.

In 2004 Vettriano set up a scholarship for University of St Andrews to fund a student who would not otherwise be able to attend university. The scholarship is awarded every four years. The endowment follows his financial contribution towards refurbishing the Students Association’s Old Union Coffee Bar in 2002 and his involvement in student fashion shows. He was made a Doctor of Letters by the university.

Divorced from his first wife, Vettriano divides his time between homes in London, Kirkcaldy and Nice, France. In 2004, he was awarded the OBE. He claims he has drawn inspiration for his paintings from “25 years of sexual misbehaviour”. In 2010, he told The Independent: “I live in a world of heartbreak… I just seem to be more creative when I’m in some kind of emotional distress”, adding “It’s been four years of soul-searching – nicotine, alcohol, anti-depressants, temazepam”.

In October 2005, after the original of The Singing Butler sold for £740,000, it came to light that Vettriano had used the artists’ reference manual The Illustrator’s Figure Reference Manual to form his figures, using Irish actress Orla Brady for the ‘lady in red.’

Vettriano has studios in Scotland and London. He was represented by the Portland Gallery, London from 1993 to 2007, and counts Jack Nicholson, Sir Alex Ferguson, Sir Tim Rice and Robbie Coltrane amongst his collectors. To date, five books have been published about Jack Vettriano, the most recent of which, Studio Life, was published in March 2008. In February 2009, Vettriano launched Heartbreak Publishing and his own London gallery, also called Heartbreak, which exclusively represents him, but still promotes younger artists.

In May 2008, Vettriano collaborated with Sir Jackie Stewart, on a triptych of paintings entitled Tension, Timing, Triumph – Monaco 1971. The paintings were unveiled by Prince Albert of Monaco at a private reception at the Hôtel de Paris in Monaco on 21 May 2008. The originals hang in Stewart’s private collection in the UK and the images have been published as a limited edition print.

Vettriano donated a portrait of Zara Phillips MBE, entitled Olympia, to Sport Relief in 2008. The painting went to a charity fund-raising auction, selling at Bonhams for £36,000. In 2010, Vettriano created a postcard – alongside names such as Tracey Emin and Florence Welch – as part of a British Airways campaign for Sport Relief. The postcard raised over £2,000.

In March 2010, Days Of Wine And Roses was opened by Scottish First Minister Alex Salmond at the Kirkcaldy Museum. The exhibition then transferred to Vettriano’s gallery in London.

On 24 March 2010, Sir Jackie Stewart presented Vettriano with the Great Scot of the Year Award. The award ceremony was held at the Boisdale Club in London. The award led MSP Ted Brocklebank to file a Motion in Parliament calling for Vettriano’s contribution to Scottish culture to be recognised.

In April 2010, seven out of ten paintings by Vettriano failed to sell at Sotheby’s spring auction of Scottish pictures. Those that sold did so for half their previous prices. Art experts suggested that the monetary value of Vettriano’s works needed reassessing.

Following on from the previous year’s event in Monaco, Vettriano was invited to create a series of paintings to celebrate the centenary of Tuiga, the Yacht Club de Monaco’s flagship yacht, which was built on the Clyde. The paintings were first shown in an exhibition, ‘Homage à Tuiga’, in Monaco and were part of a touring exhibition that opened at the Kirkcaldy Museum in Fife in March 2010.

Also in 2010, Vettriano helped to raise money for the conservation movement Elephant Family by participating in an auction of donated elephant sculptures and models. Vettriano’s elephant, The Singing Butler Rides Again, was the highest bid-for lot, selling for £155,000. Vettriano was also asked by First Minister, Alex Salmond to create his official Christmas card Let’s Twist Again. The original painting and limited-edition prints later sold at auction for the benefit of four Scottish charities, raising £86,000.

In February 2011, it was announced that Vettriano’s self-portrait The Weight would be displayed at the re-opened Scottish National Portrait Gallery from November 2011, the first time he had exhibited at a national gallery. Deputy director Nicola Kalinsky said Vettriano was “a figure we have wanted on our wall for a while for obvious reasons”. First Minister, Alex Salmond said of Vettriano, “He is a wonderful artist of considerable talent and achievement and this is a magnificent tribute to the special place he holds in the hearts of people in Scotland.”

In May 2011, ‘The Ballroom Spy’ exhibition opened at Vettriano’s gallery Heartbreak – a new exhibition by Vettriano in collaboration with the photographer, Jeanette Jones. In July 2011, the exhibition transferred to the Royal West of England Academy in Bristol, which was viewed as a controversial choice by many.

Vettriano worked with the Italian photographer Fredi Marcarini, both on a series of photographs for the ‘Homage à Tuiga’ exhibition and on a triptych of portrait shots. In May 2011, Vettriano collaborated on the exhibition ‘The Ballroom Spy’ with the photographer Jeanette Jones.

In January 2012, menswear brand Stefano Ricci launched its Spring Summer 2012 collection with a campaign inspired by the work of Jack Vettriano. The SS 2012 catalogue, entitled ‘Stefano Ricci – a tribute to Vettriano’, featured images by Vettriano and photographic re-interpretations shot by Fredi Marcarini featuring clothes and accessories from the Ricci 2012 collection. A short film about the 2012 Vettriano campaign commemorated the collaboration.

In February 2012, Vettriano’s most famous painting, The Singing Butler, went on display at the Aberdeen Art Gallery as part of an exhibition entitled, ‘From Van Gogh to Vettriano’.

In 2012, Vettriano was convicted on alcohol and drug charges, and given an £800 fine for possession of amphetamines and an 18-month driving ban.

In September 2013, a major exhibition, ‘Jack Vettriano: A Retrospective’, opened at Glasgow’s Kelvingrove Art Gallery and Museum. It featured over 100 works and ran until 23 February 2014.

In 2013 in The Guardian, art critic Jonathan Jones wrote: “Vettriano fixes on fetishistic, stylish objects and paints them with a slick, empty panache” and “The world of Jack Vettriano is a crass male fantasy that might have come straight out of Money by Martin Amis”.

In 2015, a private collection of 12 works by Vettriano raised a total of £837,900 at an auction in Edinburgh.

In 2017, he was one of three artists commissioned to paint portraits of Scottish comedian Billy Connolly to celebrate Connolly’s 75th birthday. These were then put on display in Glasgow’s People’s Gallery, while the images were transferred to murals in the centre of Glasgow. Vettriano’s mural is located in Dixon Street, off St Enoch Square. It was the subject of a BBC Scotland documentary first broadcast on 14 June 2017.

In 2018, Worthing’s Room With A View gallery showcased 30 Vettriano paintings. Art dealer Jane Hill stated that Vettriano is “self-taught which I admire immensely. He has really pulled himself up from the depth of nowhere.”

In collaboration with fellow Fife native Stephen Anderson of Commercial Spirits, Vettriano launched Jack Vettriano Gin, a spirit product featuring four of Jack’s paintings: The Singing Butler, Billy Boys, Along Came A Spider & A Kind Of Loving. The brand was launched at the Forth Floor Bar & Restaurant in collaboration with Louise Masson, GM of Harvey Nichols, Edinburgh with an auction of four signed giclee paintings raising over £7000 for charity Bottle sets of #1, #2 and #3 were donated to the ‘Lunch With an Old Bag,’ a charity auction on 7 September 2018 at Prestonfield House in Edinburgh