- Was rejected by Toronto's Second City branch, so he moved to Chicago and studied comedy with the original Second City troupe and with iO.
- Joined Chicago's Improvised Shakespeare Company during its initial season in 2005.
- Garnered millions of views for his I'm Into Nuggets, Y'all rap video.
- Was featured in Upright Citizens Brigade's improvised comedies Diamond Lion, Baby Wants Candy and Gravid Water.
- Landed the lead in the 2009 romantic-comedy Splinterheads.
- In 2011 Variety named him as one of their 10 comics to watch.
- Has been featured in numerous comedy videos on the College Humor Web site.
- Self-released the music CD Semi-Serious.
- 2015, Critics' Choice Television Awards — Best Actor in a Comedy Series: Nominee
- 2016, Emmy — Outstanding Lead Actor in a Comedy Series: Nominee
- 2017, Critics' Choice Awards — Best Actor in a Comedy Series: Nominee
- 2014, Critics' Choice Television Awards — Best Actor in a Comedy Series: Nominee
- Attended George Brown College School of Performing Arts, Toronto, Ontario, Canada
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