In The stilt race we see the introduction of Smart’s archetypal motifs – road signs and markings in the zebra crossing and the turning arrow. The urban setting combined with the two figures teetering on stilts – inspired by a photograph Smart had seen of an African tribe – makes for a work with a surrealist inflection.

The stilt race was one of two paintings selected for inclusion in the groundbreaking Recent Australian Painting exhibition at Whitechapel Gallery in London in 1961. Buoyed by this international recognition of his work, by 1963 Smart felt he was ready to move to Italy permanently.

The idea for this painting grew during a visit to Australia. While driving around Sydney with fellow artist Michael Ramsden one Sunday morning, Ramsden suddenly stopped the car at Central Railway Station and ran off to buy the morning paper. Smart caught a glimpse of him running between hoardings constructed over an unfinished pedestrian tunnel under George Street. Struck by this vision in the morning light, Smart returned to this location early the following morning to make drawings and sketches, from which the final picture was painted when he returned to Italy.

The most prominent motifs of Smart’s later works are roadways and apartment blocks. When he first arrived in Rome, he lived near the EUR district. This area was characterised by a striking mix of Fascist era apartment blocks, architectural relics, hoardings, office buildings and open fields. Smart developed a fascination for the new cityscapes that swept through Italy as the postwar economic boom took hold, changing the visual landscape of the country. He also encountered Italy’s motorways – beautiful structures curving through the mountains with arresting traffic signage.

Truck and trailer approaching a city evokes a sense of urban alienation. Smart utilises colour, scale and uniform geometric shapes to portray the anonymity of a group of apartment buildings that span the horizon of this painting as a removalist truck approaches the urban centre.

During a visit to the Louvre in Christmas of 1993 Smart noticed a long temporary wooden screen in an empty gallery and thought the geometry, light and shadows of the space would make a wonderful picture.

Back in his Tuscan studio he worked up studies of the Louvre scene that included two figures walking through the space, but he decided he needed a static figure to anchor the composition. ‘I thought if I’ve got to have a static figure, it may as well be a portrait of someone and then I thought of Margaret,’ he stated. Smart commissioned Australian photographer Robert Walker to photograph Olley and from these photos and his initial sketches, he created this painting.

Olley later said of this work, ‘I’m more at home in the Louvre than standing on one of Jeffrey’s freeways or empty car parks’.

Smart’s Matisse at Ashford is perhaps the finest work of his later years. Like many of his paintings, it found its origin in a passing glance while he was sitting on a train in England. He recalled:

…while the train paused at Ashford Station, just after the tunnel, I was given the most heavenly theme … billboards, which … have one of Matisse’s spiritually barren motifs on them.

He was referring to banners advertising a Matisse exhibition at the Royal Academy in London, featuring one of Matisse’s famous blue cut-out nudes. Before the train moved off, Smart quickly made sketches on the endpapers of a novel. The work was further developed in his studio over the ensuing months through a succession of studies.

Sometimes Smart’s work was built upon an idea or a memory of something viewed long ago. A jungle gym first appeared in the background of a 1989 painting The new school, and a sketchbook from the same year. This motif remained in Smart’s mind and in late 1997 he decided to paint a children’s playground, featuring a jungle gym as the central subject. Smart spent time seeking a jungle gym around Arezzo to draw but was unable to find any. He contacted his archivist Stephen Rogers in Australia, but he was also unable to find one. Smart then decided to commission a computer-generated image instead.

Smart was meticulous in his requirements, asking that the scene of the structure be set on 13 October 1997 at 4.30pm at 43 degrees latitude with the viewer standing three meters away from the structure. When he received the finished computer generated drawing, he was delighted and worked up the painting through a series of studies.

This work is an excellent example of how Smart constructed an image of a scene that didn’t exist, utilising technology to achieve his perfect vision.

In this portrait of Australian expatriate author and journalist Clive James, the sitter is reduced to a tiny blip on the horizon, dwarfed by skyscrapers and a yellow corrugated iron fence.

The development of this work spanned many studies and versions. Smart began by using a stand-in model to place his subject in an urban setting resembling a carpark, and he made some detailed head studies to establish facial features.

After making several studies of James, Smart decided the composition wasn’t working and so scrapped the in-progress work in favour of a new scene featuring a yellow fence he had viewed from a train in Tokyo. Smart placed James into the Japanese setting, diminutive in scale and set back far behind the fence. As in all of Smart’s works featuring figures, James’ tiny form in this sizeable painting acts as a measure of scale.