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Cherry Pie, Moyna Flannigan, 2004, oil on linen

Painting portraits is what Edinburgh-based artist Moyna Flannigan does. For many years, she has focused on this genre. But not in the traditional sense—the people that populate Flannigan’s works are imaginary—an amalgamation of memories, people watching and remembered images from books and magazines. In her last solo show, she contemporarised the portrait miniature. Once Upon Our Time, 2004, housed in the grand neo-Gothic Scottish National Portrait Gallery, featured 50 make-believe characters, exquisitely painted as small-scale portraits on vellum. These were shown alongside a selection of the National Galleries’ collection of miniatures dating from the early 16th century to today. One year on, in the heart of Chelsea, home to a cluster of New York’s most important look-alike white-box contemporary galleries, Flannigan is back for a third solo show at Sara Meltzer.

A Pie in the Kisser, is a fitting title for this exhibition of new paintings and pastel works on paper, again of imaginary individuals. Slapstick humour is ever present as the title suggests, but there is a dark undertow in equal measure. In the first space six large-scale oil paintings take a confrontational stance. A transvestite stares at his ageing reflection in the mirror in ‘The Silent Apprentice’. A woman sits in wait, legs open, in ‘Ready for the Close-up’. A bare-bottomed woman in thigh-length boots steps over a bare-bottomed man on all fours in ‘A Pie in the Kisser’.

It feels wrong or uncomfortable to laugh. The characters may well call to mind saucy seaside postcards, a Les Dawson sketch or worse still, Bette Davis in What Ever Happened to Baby Jane, but as so often with the best humour, each gag has been forged from alienatation or sadness. Flannigan’s exaggerated portraits explore serious issues, with personal, cultural and political isolation being top of that agenda. The dominatrix who has no-one to dominate, the lone ‘Baby Jane’ character propping up the bar, or the wide-eyed woman in yellow, all dressed up and nowhere to go, all illustrate her concerns. These ‘misfits’ or ‘oddballs’, who would otherwise provoke a snigger or sneer ask to be understood in Flannigan’s portraits.

A Pie in the Kisser underlines Flannigan’s status as one of Scotland’s most interesting figurative painters. Recently presented with a Creative Scotland Award, worth £30,000, she plans to use the funding to create a series of fictional portrait paintings which explore modern-day parallels to the political dynasty of Bonnie Prince Charlie.

Helen Monaghan is an art writer, and talks and events programmer at the National Galleries of Scotland, Edinburgh