Are you ready for a double dose of the man whose name has become synonymous with cynicism and manipulation? Canberra playwright and director Rachel Hogan is presenting a theatrical double bill of Niccolo Machiavelli that she says shows how relevant and entertaining his works remain 500 years after they were written.

The first play is a comedy, Hogan's adaptation of Machiavelli's hit play La Mandragola (The Mandrake Root). In it, the young playboy Callimaco (played by Brendan Kelly) lusts after the virtuous Lucrezia (Jess Waterhouse), who is married to Nicia (Philip Meddows). Callimaco's friend Ligurio (John Lombard) comes up with a scheme to bring this about. They remain childless and Nicia is desperate for a son, so Callimaco poses as a French doctor specialising in female fertility, which he says can be restored by means of the mandrake root.

"The only problem is it's poisonous and the poison passes on to the next man she has sex with – who could that be?"

With a cougar-like mother of the wife (Nikki-Lynne-Hunter), a corrupt confessor (Tony Cheshire) and a busy and possibly crooked servant Sira (Hogan's husband, Peter Fock) – a character Hogan says was based on the author himself – also involved, the scene is set for a cynical farce that has remained popular and performed for centuries.

"I tried to stick to Machiavelli's structure," Hogan says. She made some changes, trimming some parts and fleshing out the female characters, who were thinly drawn by Machiavelli in a way that modern audiences would not find appropriate.

"I think he would approve of the changes I've made – I've given them more of an arc."

The second play of the evening is a reworking of her one-act play The Prince, written eight years ago for the Festival of One-Act Plays, where it won awards for best actor and best original script. Fock plays Machiavelli himself at about the time he wrote The Mandrake Root and his political treatise The Prince. He was out of favour, recently out of prison and exiled from Florence after the Borgias, for whom he had worked in government, were overthrown.

Just as the real Machiavelli did, he locks himself in his study and conducts urgent philosophical debates about power and morality with famous dead men – including Hannibal, Plato and Cesare Borgia – in an imaginary court presided over by the Devil, until his wife Marietta (Nicola Tyndale-Biscoe) fears for his sanity.

"She works her way up to confronting him about him what happened to him in prison."

They discuss some of the contradictions inherent in his positions. He was a Republican whose most famous work, The Prince, was written as a job application to the Medici court – "Here is how good I am when I go out out in the world" is how Hogan describes this treatise on power. It was the victorious Medicis who had had him tortured while he was imprisoned while accused of conspiracy against them – yet he still supported torture in certain circumstances.

Hogan has long been interested in the Renaissance, a rich period of history and culture for both good and ill. And while Machiavelli may have been cynical about love, he led to at least one marriage.

"The Prince was the first thing Peter and I worked on – we fell in love while we were doing it."