[citation needed] Della Siepe attended York Memorial Colligate Institute in Toronto, where he excelled in the drama program and was involved in many school productions.
[citation needed] In his early years he idolized Jim Carrey, and from the age of 12 he had aspirations of becoming a stand-up comedian.
Della Siepe is a national touring headliner and a regular in the Toronto comedy scene.
[citation needed] In 2009 he co-starred in all 20 episodes of MuchMusic's reality dating show Love Court, hosted by Canadian recording artist Elise Estrada.
[2][7][8][9] In 2004 Della Siepe was cast as a lead in the modern-day war drama American Soldiers by Hollywood director Sidney Furie.