| Year | Award Ceremony | Category | Nominated work | Result | Ref. |
| 2015 | International Online Cinema Awards | Best Writing for a Comedy Series (shared with Charlie Day and Rob Mac) | It's Always Sunny in Philadelphia | Nominated | |
| 2019 | IGN Summer Movie Awards | Best TV Ensemble (shared with Charlie Day, Rob Mac, Kaitlin Olson, and Danny DeVito) | Nominated |
| 2023 | Chicago Film Critics Association Awards | Best Supporting Actor | BlackBerry | Nominated |
| Gotham Awards | Outstanding Supporting Performance | Nominated |
| Hollywood Film Critics Association Midseason Awards | Best Supporting Actor | Won |
| Indiana Film Journalists Association | Best Lead Performance | Nominated |
| Las Vegas Film Critics Society Awards | Best Supporting Actor | Nominated |
| North Texas Film Critics Association | Won |
| Toronto Film Critics Association Awards | Outstanding Supporting Performance | Runner-up |
| Outstanding Performance in a Canadian Film | Won |
| UK Film Critics Association Awards | Supporting Actor of the Year | Nominated |
| 2024 | ASTRA Awards | Game Changer Award | Won |
| Best Supporting Actor | Nominated |
| Canadian Screen Awards, CA | Performance in a Supporting Role, Comedy | Nominated |
| Chicago Indie Critics Awards | Best Supporting Actor | Nominated |
| Columbus Film Critics Association | Best Supporting Performance | Nominated |
| DiscussingFilm Critic Awards | Best Supporting Actor | Nominated |
| Georgia Film Critics Association | Nominated |
| Independent Spirit Awards | Best Supporting Performance | Nominated |
| Music City Film Critics' Association Awards | Best Supporting Actor | Nominated |
| Online Film & Television Association | Best Breakthrough Performance: Male | Nominated |
| Vancouver Film Critics Circle | Best Supporting Male Actor in a Canadian Film | Won |
| Canadian Screen Awards | Best Supporting Performance in a Comedy Film | Won | |