[25] Smiles' stage plays focus largely on biographical subjects such as Spike Milligan (Ying Tong - A Walk With The Goons), Kurt Cobain (Kurt & Sid), Albert Camus (The Weight Of Days), Evelyn Waugh (Waugh In Winter), Marilyn Monroe/Arthur Miller (Reno),[26] George Orwell (Year of the Rat),[27] Tony Hancock (The Lad Himself)[28] & Robert F. Kennedy (The Last Pilgrim).

[29] His first play staged in 1992 at the Battersea Arts Centre, Schmucks[30] was about a fictitious meeting between Groucho Marx and Lenny Bruce.

[31] A number of his plays have debuted or transferred to theatres around the world, such as Pythonesque,[32] the story of the Monty Python team, which opened in South Africa in 2008 before moving to Edinburgh as part of the Fringe Festival in 2009.

It was revived at The Kings Head Theatre in 2006 under the title The Ho-Ho Club directed by Karl Howman and starring Sally Lindsay.

[42] Good Evening - about the Beyond The Fringe team had its world premier in South Africa in 2007 then was broadcast on Radio 4 in 2008, with Benedict Cumberbatch as Dudley Moore.

[46] Reno - his play about Marilyn Monroe & Arthur Miller's marriage imploding during the making of The Misfits had its world premiere at the Brighton Festival in 2014.

Containing his plays on Albert Camus, Richard Burton, Oscar Wilde/George Bernard Shaw, Evelyn Waugh, Tony Hancock, Lenny Bruce, the Enola Gay, the Iraq War, Marilyn Monroe/Arthur Miller & the 2011 London Riots.