| Year | Award | Category | Work | Result | Ref |
| 2009 | John Hirsch Award | Most Promising Young Actor, Stratford Festival | Morris Panych's Trespassers | Won | |
| 2011 | ACTRA Awards | Outstanding Performance – Male | Score: A Hockey Musical | Nominated | |
| 2016 | Canadian Screen Awards | Achievement in Music – Original Song | People Hold On (Song: People Hold On) | Nominated | |
| 2017 | My Entertainment World Critics' Picks Theatre Awards | Outstanding Supporting Actor (Medium) | Jasper, Annie Baker's The Aliens at The Coal Mine Theatre | Won | |
| 2018 | Canadian Screen Awards | Best Supporting or Guest Actor, Comedy | Schitt's Creek, Season 3 | Nominated | |
| 2019 | ACTRA Awards | Members' Choice Series Ensemble | Schitt's Creek, Season 4 | Won | |
| Canadian Screen Awards | Best Supporting or Guest Actor, Comedy | Schitt's Creek, Season 4 | Won | |
| Dorian Awards | TV Musical Performance of the Year | Schitt's Creek (Performance: Simply the Best) | Nominated | |
| Screen Actors Guild Awards | Outstanding Performance by an Ensemble in a Comedy Series | Schitt's Creek, Season 5 | Nominated | |
| 2020 | ACTRA Awards | Members' Choice Series Ensemble | Schitt's Creek, Season 5 | Won | |
| Canadian Screen Awards | Best Supporting Actor, Comedy | Schitt's Creek, Season 5 | Nominated | |
| Dorian Awards | TV Musical Performance of the Year | Schitt's Creek (Performance: Always Be My Baby) | Nominated | |
| Screen Actors Guild Awards | Outstanding Performance by an Ensemble in a Comedy Series | Schitt's Creek, Season 6 | Won | |
| 2021 | ACTRA Awards | Members' Choice Series Ensemble | Schitt's Creek, Season 6 | Won | |
| Canadian Screen Awards | Best Supporting Actor, Comedy | Schitt's Creek, Season 6 | Nominated | |
| 2022 | Canadian Folk Music Awards | English Songwriter(s) of the Year | Gemini | Nominated | |
| Canadian Folk Music Awards | New/Emerging Artist(s) of the Year | Gemini | Nominated | |
| 2023 | Heritage Toronto | Public History Award | The History of the Danforth Music Hall | Nominated | |
| 2025 | Toronto Theatre Critics Awards | Best Lead Performance in a Play | A Case for the Existence of God | Won | |
| Dora Awards | Outstanding Performance by an Individual | A Case for the Existence of God | Nominated | | |