Opportunities

Known for his razor-sharp wit and intelligent social commentary, Jeremy Elwood is one of New Zealand’s most respected comedians and broadcasters. Born in Canada and raised in Dunedin from his teenage years, Jeremy completed both his high school education at Otago Boys' High School and later university studies in the city before launching a comedy career spanning more than two decades. A regular face on television and radio, he has appeared on shows including 7 Days and The Project while performing across New Zealand and internationally.

Jonathan Lemalu is one of New Zealand’s most celebrated opera singers and an internationally acclaimed bass-baritone whose career has taken him to some of the world’s leading concert halls and opera houses. An OBs Old Boy, Jonathan discovered and developed his love of music in Dunedin before continuing his studies and launching a remarkable international career. He has performed with leading orchestras and opera companies across Europe, North America and Australasia, earning widespread recognition for both his powerful voice and stage presence.

Colin McCahon is widely regarded as one of New Zealand’s most influential artists, known for his bold, thought-provoking works that explored landscape, spirituality and national identity. McCahon’s early years in Dunedin helped shape the creative foundations that would later define his work. Over a career spanning decades, his paintings challenged artistic conventions and helped transform modern art in New Zealand.

Brent Alexander is an Old Boy whose career has spanned architecture, business, music and community leadership. After attending OBHS from 1977–1981, Brent built a successful career in design and construction, founding an award-winning Dunedin architectural practice while becoming well known for his work across residential and commercial design. Beyond business, he was also drummer for iconic Dunedin band the Netherworld Dancing Toys during the height of the Dunedin music scene. A passionate supporter of the school, Brent has also played a significant leadership role within the Old Boys’ Society and wider OBHS community.

Hamish Kilgour was an influential musician, songwriter and visual artist best known as a founding member of the iconic Dunedin band The Clean. Hamish helped shape what would become known internationally as the “Dunedin Sound” - a raw, melodic style that influenced generations of musicians around the world. Through The Clean and later musical projects, his creativity earned a cult following both in New Zealand and overseas. Beyond music, he was also an accomplished visual artist, with his work reflecting the same distinctive creativity that defined his career.

John Grenell was one of New Zealand’s most successful and recognisable country music artists, building a career that spanned more than five decades. Raised in Central Otago and Dunedin, John developed his love of music while at OBHS before launching a remarkable recording career. Known for hits including I’ve Been Everywhere and Welcome To Our World, he became one of New Zealand’s highest-selling recording artists and performed across New Zealand and internationally. His distinctive voice and authentic rural style made him a true icon of New Zealand country music.