His most recent stint in Ngawha's Northland Region Corrections Facility came after he was sentenced in 2013 to six-and-a-half years' jail for burglary and theft from a Dargaville ATM, which netted $112,000.
He had been on the run for two years when he was arrested and was granted parole on October 5 this year. As part of his parole conditions he is not allowed to enter Whangarei, Auckland or Dargaville, meaning he will need special permission if he wants to view his exhibition.
Sheree Edwards, exhibition curator and owner of Jetsom Artspace in Kerikeri, has acted as an artistic mentor to Mr Kerr since she first saw his work early this year.
"I immediately fell in love with his raw natural talent and these incredibly dramatic and bold paintings, and also the determination of Simon and [his partner] to better their lives," she said.
Mr Kerr had previously exhibited at No.1 Parnell Gallery; Depot Artspace in Devonport; and is showing pieces at Jetsom Artspace as part of its Emergent exhibition.
He is working towards a solo exhibition at Jetsom in January.
"He has the ability to communicate his life experiences in a raw and honest way," Ms Edwards said. "His works are dark and playful, spontaneous yet purposeful, with the important element of self-reflective humour."
Mr Kerr said he was less interested in learning the technical side of painting.
"I don't have any desire to be a painting expert. In fact, I am active in dodging that bullet. I don't want to copy things or lives for that matter. For better and worse I have my own life story to tell and my own observations of the world to blurt out," he said.