Keeso starred as hockey coach, player, and commentator
Don Cherry in two
CBC television movies about Cherry's life. The first,
Keep Your Head Up Kid: The Don Cherry Story, aired in early 2010, and was followed by
The Wrath of Grapes: The Don Cherry Story II in 2012. For his performances, he won a
Leo Award for Best Lead Performance by a Male in a Feature Length Drama and a
Gemini Award for Best Performance by an Actor in a Leading Role in a Dramatic Program or Mini-Series. In 2013, Keeso and Mike Borden created Play Fun Games Pictures on
YouTube. The channel became an immediate success thanks to a series of shorts sketches depicting the quintessential Canadian farmer and the associated struggles. The series,
Letterkenny Problems, has attracted over 100 million views (), and became the basis for the hit 2016 sitcom
Letterkenny. The sketches and TV series are both shot in
Sudbury, Ontario. In 2014, Keeso starred in a
Heritage Minute about the
Winnipeg Falcons, a team of Icelandic-Canadian hockey players who served in the
First World War, and later won the country's first
Olympic gold medal in hockey. Following the cult success of
Letterkenny, in 2022 Keeso created a spin-off series
Shoresy, focusing on the titular character of
Shoresy which is also set and shot in Sudbury. Keeso has had a variety of other roles in both television series and movies, including as Ben Chartier in the 2014
English-language adaptation of 19-2, for which he won a
Canadian Screen Award for Best Performance by an Actor in a Continuing Leading Dramatic Role. He also has less prominent roles in a few other films, such as Nicholas in ''
Smokin' Aces 2: Assassins' Ball; Adam in the high-school themed Lifetime original movie Seven Deadly Sins
; and Simon in the drug-themed Charlie''. ==Filmography==