In high school, he hosted a student-produced TV show called You Can't Do That on Channel One.
As a teen, sold Christmas trees for three holiday seasons.
After moving to Los Angeles, he joined the famed Second City comedy troupe.
Was discovered by Will & Grace star Megan Mullally while he was performing at a comedy club with the group Animals from the Future; she later recommended him to SNL's Lorne Michaels.
Worked as a field agent on MTV's Punk'd.
Received a 2012 Emmy nomination for Outstanding Supporting Actor in a Comedy Series; with his nomination he became Saturday Night Live's first male cast member since Eddie Murphy in 1983 to receive a nod.
Left Saturday Night Live in May 2013 after eight seasons, and signed on soon after to write full-time for Comedy Central's South Park.
Became the voice of snack legend Mr. Peanut in 2013.
On a 2016 episode of Find Your Roots, discovered he is descended from Edward I of England and Charlemagne.