Keeso has had a variety of minor roles in both television series and movies, but is best known for his role as the leading character Ben Chartier in the English adaptation of 19-2, for which he won the Canadian Screen Award in 2015 for 'Best Performance by an Actor in a Continuing Leading Dramatic Role'; and for his starring role in two Canadian biographic films of legendary hockey commentator Don Cherry, for which 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'.