Gavin McInnes' was one of the founders of the boundary-pushing magazine Vice in the 90s.
But fast forward a couple of decades and he is starting and leading the Proud Boys - a far-right, neo-fascist group that played a key role in the January 6 attack on the US Capitol.
The question of what led to that drastic swing is at the heart of Thomas Morton's documentary It's Not Funny Anymore: Vice to Proud Boys.
Thomas was a cub journalist at Vice and looked up to McInnes and others at the magazine popular with millennials for its focus on underground societies.
He followed McInnes's life after Vice and has interviewed family and friends of the man he calls his first mentor in writing and journalism.
The film builds up to a showdown interview between the two at the end as Thomas tries to understand why his big brother figure became so extreme.
Photo: Supplied by Urbania
