Jackson graduated with BA (Hons) in Fine Art Sculpture from the Chelsea College of Art and Design as an adult student. Here she established herself as an abstract painter with a difference, completing a small number of critically acclaimed works. Soon after, in 1997, her graduation piece, Crucifix, was the first exhibit in a new South London gallery, and was priced at £1,500 (five years later valued at ten times that amount). Jackson went on to gain her MA in Fine Art Photography from the Royal College of Art, London.

She became notorious in England in 1999 for producing black-and-white photographs including images that apparently showed Princess Diana and Dodi Al-Fayed with a mixed-race love child. The photographs were part of her graduation series entitled Mental Images. She has gone on to produce similarly obscured photos and films of celebrity look-alikes in surprising, shocking or strange situations, portraying them, as she has described it, 'depicting our suspicions'.

She was the artist behind BBC Two's series Doubletake, for which she won a BAFTA. She has recently depicted George W. Bush and Tony Blair lookalikes in a series of 'behind the facade' scenes, and has produced a film devoted to the latter which coincided with his exit from office entitled Blaired Vision, shown on Channel 4 on 26 June 2007. She is launching a new online celebrity news site soon, and is developing a new series for American television, and finishing a book for Taschen featuring 300 of her images.

She is also an Ambassador to the Spinal Injuries Association.