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Jonathan Ogilvie began his creative journey in the post-punk music scene of Christchurch, producing moody music videos for Flying Nun bands like The Jean-Paul Sartre Experience and Headless Chickens. His iconic 1987 video for Straitjacket Fits' "She Speeds," filmed on a truck in the Lyttelton tunnel, was made for just $250. After earning a Bachelor of Arts from Canterbury University, Ogilvie worked in special effects on Kubrick’s Full Metal Jacket before graduating from the Australian Film, Television and Radio School in the early 1990s.

Ogilvie's early career included directing music videos for Australian bands and commercials, along with award-nominated videos for Headless Chickens.

In 2024, Ogilvie's fourth feature, Head South, premiered at the International Film Festival in Rotterdam. The film reflects his roots in the late 1970s Christchurch music scene. As a long-time directing teacher at the Australian Film, Television, and Radio School, he also contributes as a reader and assessor for the New South Wales Film and Television Office.