[7] Describing how she decided to become an artist and what inspired her, Vine said a "wonderful ex-boyfriend" called Ross had always told her she should become a painter, and that she had always made "crazy doodles".
Vine said it was difficult to tour with a small child but earned her Equity Card by performing with Durham Theatre Company.
[4] Vine said she would wake up early and dance to songs by PJ Harvey before improvising around her character to prepare for each day's rehearsals.
[4] In 1995,[6] she abandoned her ambitions to be an actress and became a hostess in a Mayfair club, where most of the activity was talking, often to elderly men, and "Any negotiation for sexual favours, or your time, or conversation, was very old-fashioned.
[10] She worked as a stripper at Miranda's[10] and later at the Windmill Club in Soho to pay the rent, whilst living with her son in bedsits.
[10] One man she met, whom she described as a "sugar daddy"[3] and with whom she was still in contact in 2007, looked after her for six years, and in 1998 took her to New York, where he introduced her to the Frick Collection.
[17] Vine developed a "crush" on artist Billy Childish, and attended his music events;[10] in June 2000, she went to a talk given by him and fellow Stuckist co-founder, Charles Thomson, on Stuckism.
[26] In October 2006, The Stuckist group show, Go West, at Spectrum London gallery, included two paintings by Thomson, which were "explicit images of his ex-wife.
[29] In 2002 – 2003, Vine studied Philosophical Aesthetics with Johnathan Lahey Dronsfield at Birkbeck College whilst also attending the course Performance After Warhol with Professor Gavin Butt in 2002, and Women's Work with Kathy Battista at Tate Modern.
[8] In 2003, Vine opened the Rosy Wilde gallery on Whitecross Street in east London, as a space that held exhibitions of contemporary art by emerging artists.
[6] The gallery was on the verge of bankruptcy, when Charles Saatchi purchased Vine's painting of Diana, Princess of Wales Hi Paul can you come over I'm really frightened.
In 2006, she re-opened her Rosy Wilde gallery, this time in Wardour Street[31] on the first floor above the first Ann Summers sex shop in Soho, London.
The work's title came from the thick red text painted across the canvas, a reference to Diana's butler Paul Burrell.
[25] The price of her paintings "doubled virtually overnight",[34] and as Saatchi anticipated, much of the media attacked the work in his New Blood exhibition, creating a considerable return in publicity for his investment.
[40] In September 2004, Vine threatened suicide if her work was included in The Stuckists Punk Victorian show at the Liverpool Biennial; the owner of the painting withdrew it.
[42] Vine refused to acquiesce to the parents and police's request not to exhibit the painting, then on view in the Saatchi Gallery in the New Blood show during March 2004.
Richard Dorment, The Daily Telegraph critic, described the work as "another stab at creating the visual equivalent of tabloid journalism.
One painting called The Rumbling Kurn (2003) shows part of the Alnwick shoreline near Howick beach, whilst 27 Clayport Gardens (2004) depicts Vine in a pram as a child "outside her grandmother's old house".
At this time, Vine collaborated with the artist James Jessop for the exhibition Fame at the This Way Up Gallery above the Dragon Bar in East London.
The installation of paintings was based on the New York graffiti scene of the 1980s, including depictions of Fab Five Freddy, Keith Haring and Blondie.
[54] In the February 2009 issue of Gay Times, Vine discussed the 'tabloid frenzy' and media scrutiny that followed Saatchi collecting her work in 2004: "In the beginning it was a real battle to assert any kind of intelligence at all.
[50] In June 2006, Vine held a solo show at the Bailiffgate Museum in Alnwick called Whatever Happened to Melissa Jane?.
[60] In August 2006, she was featured in the tabloids, when her painting of Celebrity Big Brother stars, Samuel "Ordinary Boy" Preston and Chantelle Houghton, "was used as the invitation to their wedding".
[3] and oversaw the set up and installation of her exhibition at the museum herself, though did not attend the opening press launch day or any of the private view evenings.
[64] Richard Dorment of The Daily Telegraph praised Vine's work in the show for its ability to "skewer celebrity culture with a vitality and truth that can't be faked".
[64] Lynn Barber, writing for The Observer described Vine as "the real deal",[3] and Paul Moody praised her work for "causing a storm in the art world".
[66] Arifa Akbar of The Independent compared Vine's examination of the culture of celebrity as coming from the same tradition as pop art founder, Andy Warhol.
[67] In July 2007, Vine collaborated with Topshop clothing chain, creating a limited edition fashion range inspired by her artworks.
[66] In November 2008, it was announced that Vine had begun painting a series of new work for a large solo show at the Eden Project, Cornwall, England to be held in 2010.
[69][needs update] In 2005, Stella Vine gave three paintings to the Imagine A World exhibition, organised by Amnesty International.