British director Michael Winterbottom would have to be one of the most relentlessly ambitious directors working in film today, constantly jumping between wildly different projects over the past 17 years.

Set in Norway’s infamous Bastøy Prison, once a reformatory prison colony for delinquent boys, The King of Devil’s Island depicts the lead up to a series of riots that took place at the facility during the early part of the 20th century.

Interiors holds the distinction of being Woody Allen’s first entirely dramatic work, and while he has explored more serious subject matter in other parts of his later career, this was a marked shift from the screwball comedies of his early years.

Another in a long line of slight romantic comedies to be exported from France, Romantics Anonymous in short might be best described as a cross-pollination of Amelie and Chocolat: a mixture of unbridled whimsy with endless amounts of chocolate.

Often regarded as the original contemporary romantic comedy, Woody Allen’s Annie Hall has endured to be one of the most popular and critically acclaimed films from his incredibly prolific career.

Woody Allen and Diane Keaton teamed up again for this follow up to 1973’s Sleeper, respectively starring as Russian peasants Boris and Sonja, set during the Napoleonic Era. While ostensibly another absurdist comedy from Allen, this film’s blending of references to philosophy,

Rustic Setting. Era-Appropriate Clothing and Music. Measured and Thoughtful Pace. Daniel Auteuli’s The Well Digger’s Daughter, an adaptation of the 1940 film of the same name by Marcel Pagnol, ticks all of the expected boxes in this workmanlike period melodrama set during the early stages of the Second World War.

It was only a matter of time until American filmmakers began to turn their attention to the events surrounding the global financial crisis of 2008, and writer/director J.C Chandor’s  feature debut is probably the strongest one to emerge so far.

Director Jonathan Levine follows up 2008’s The Wackness with 50/50, a relatively low-key ‘dramedy’ starring Jason Gordon Levitt and Seth Rogen.

Leonardo Live is being screened as a special event by a number of Australian cinemas on Saturday 18 and Sunday 19 February.