– Little Sparta (1966-2006)

The artist and poet Ian Hamilton Finlay created Little Sparta, Scotland’s most ambitious permanent installation, as a modern meditation on the themes of 18th-century landscape gardening. Classical inscriptions and sculpture mingle with disturbing allusions to warfare and violence – the lethal arrows of Apollo, Pan and Panzer tanks – in this neo-pastoral masterpiece of conceptual art.

Alasdair Gray – Illustrations to Lanark (1982)

The prophet of Scottish independence? Politics aside (although you can’t really separate Alasdair Gray’s nationalist convictions from his visionary imagination) this painter and novelist is like a contemporary William Blake in his juxtapositions of image and text. His fantastic illustrations in Lanark fuse in the mind with the lucid nightmare prose of this masterpiece of metamorphosis and self-loathing.

Douglas Gordon – Confessions of a Justified Sinner (1995)

The winning work in the 1996 Turner prize was a meditation on Scottish culture and identity. Gordon’s video installation uses footage from the 1931 film of Robert Louis Stevenson’s Dr Jekyll and Mr Hyde. He slows down the transformation of man into monster, sanity into madness, so it becomes an epic of disintegration. Yet the work’s title is that of an earlier Scottish literary classic, by James Hogg, which also deals with doubles and with good and evil. These are classic Scottish themes, points out Gordon.

Henry Raeburn – Colonel Alastair Randaldson Macdonell of Glengarry (1812)

Henry Raeburn’s portraits are frank and moving. He is an artist of the Enlightenment and Romantic age, picturing people in action – a parson skating on a loch, for example – or revealing their characters with untroubled intimacy. In this portrait, proud clan identity is proclaimed through tartan by Colonel Macdonell, who was in fact a cruel landlord known for evicting his tenants.

Hill and Adamson – Alexander Rutherford, William Ramsay and John Liston (1843-1847)

Three fishermen look out of the past, their faces, poses, even personalities perfectly preserved by the camera. David Octavius Hill and Robert Adamson made a sustained photographic record of working people’s lives in the middle of the 19th century. This is a moving and powerful early use of the camera as an instrument of social progress.

JMW Turner – Staffa, Fingal’s Cave (1831-32)

I know, I know, he’s English – but Scottish landscapes deeply inspired JMW Turner. His turbulent, scary yet incredibly seductive Romantic image of a storm off the island of Staffa is one of the first depictions of a steamboat as well as a homage to Scotland’s grandeur. Turner said a storm really did strike when he took the steamer to Staffa, but then, he really liked painting storms.

Christine Borland – L’homme double (The Double) (1997)

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This troubling and thought-provoking conceptual conundrum consists of radically different portraits of the same man: the Nazi pseudo-scientist and mass murderer Josef Mengele. Christine Borland sent the same collection of eyewitness accounts of Mengele to lots of portrait sculptors, who all produced contrasting images. Which is the real man? What is the true face of evil?

Richard Wright – The Stairwell Project (2010)

Scintillating … the Stairwell Project (2010) by Richard Wright. Photograph: The Modern Institute/Toby Webster Ltd

This soaring, scintillating painted ceiling is a permanent beauty created by an artist whose delicate interventions are often intended to vanish after a few weeks. Richard Wright combines the discipline of minimalism with the sensuality of Renaissance fresco to create magical, dreamlike perspectives that pierce windows in the sky.

David Wilkie – The Village Holiday (1806-11)

In the early 19th century, this painter of everyday life rivalled Turner in public esteem. David Wilkie revived the people’s art of Hogarth for the Romantic age. If his art is difficult to get excited about now, think of it as an illustration to the great novels of his age – an accompaniment to reading Sir Walter Scott.

JD Fergusson – Café Concert des Ambassadeurs (1907)

This raw, lurid, exciting image of nightlife is plainly the work of a painter who was au fait with the latest European art. Fergusson brings the energy of fauvism and the passion of expressionism into Scottish painting. Not many English artists at the time could rival his genuine avant-garde dash.