From the time that I was little, I knew that I was related to the notorious Jewish gangster Louis "Lepke" Buchalter. My maternal grandfather was Lepke's first cousin, who looked so much like him that back in the 30s, the FBI sometimes followed him. Lepke and his thugs would hang out in my great grandfather's luncheonette in Brooklyn, despite pleas to the contrary.

The story they told my young mother was that Lepke was adopted, that he wasn't really one of them, and not even Jewish. (Still, many relatives changed their last names). She was only 5 when Lepke died in the electric chair at Sing Sing, but even as an adult, she - and the rest of her generation - still carry the family's shame and fear around being related to this ruthless killer who founded Murder Inc.

But growing up in the 70s, I was proud of my gangster blood. I relished the opportunity to brag about it, and if it upped my cool quotient, all the better. My cousins collected Lepke paraphernalia with curious excitement. We romanticized the world he lived in – gangsters killing gangsters, with Lepke at the top of the chain – and wore his name as some kind of warped badge of honor.

The truth of who Lepke was is even more elusive – he was a ruthless gangster who destroyed and took lives, but he was also by all accounts a devoted husband and father, a loyal son and brother, a starving young boy who overcame extreme poverty to become a millionaire who sponsored Jews escaping Russia. With Looking for Lepke: or 13 Ways of Looking at a Black Sheep, I'll consider all facets of who and what he was, in no way apologetic for the horrible crimes he did, but exploring the complexity of his humanity.

Inspired by Wallace Steven's poem Thirteen Ways of Looking At a Black Bird, I will approach my subject from multiple angles, through a collection of thirteen short films with various approaches to narrative – verite and interview-driven documentary, scripted re-enactment, illustration, animation and abstraction. Through Looking for Lepke… I will create a portrait of this larger than-life character through the prism of what it means to have a gangster in the family, how a family secret impacts generations, and the age-old question about where evil comes from. I will attempt to reconcile the allure of the gangster with the reality of his psychopathic brutality, and to unravel the mythology of my family's infamous black sheep.