As a child, Esmer learned English by watching Canadian television – which included programs like Sesame Street and Today's Special.

[3] Esmer attended Earl Haig Secondary School, in the Toronto suburb of North York, participating in the Claude Watson Program for gifted arts students.

However, even after leaving the university and for many years has continued to study and work with David Rotenberg, a York University professor emeritus of Theatre Studies and the artistic director of his own Professional Actor's Lab – and has said that Rotenberg was the person who allowed him to actually work on his dramatic ability without calling his comedic gifts a crutch.

His next major role came in 2009 in The Listener as Osman 'Oz' Bey, the best friend of the main character Toby Logan (played by Craig Olejnik).

[11] Starting in 2014, Esmer had regular roles in You Me Her, Private Eyes, Red Oaks, and Blindspot, once again often shooting in opposite or even the same seasons.

His instinctive improvisational style and delivery made fan-favourite Rich Dotcom what the show creator Martin Gero said was the character that defined the series.

[13][14] Esmer also had a memorable 3-episode arc as Emir Kaplan, the travel blogger who broke Stevie Budd's heart, in season five of the Emmy Award-winning comedy series Schitt's Creek.

In 2015, he played a supporting role in sex comedy How to Plan an Orgy in a Small Town, directed by Jeremy Lalonde, again serving as executive-producer.

[20] Ennis Esmer is both publicly and privately involved in many charities, focusing on homelessness, poverty, sick children, and reading (particularly in the Greater Toronto area).