Improv Jackson started his improv career with River City Improv, a group associated with Calvin University, after attending a rehearsal to play the piano. Jackson later joined
The Second City Detroit, becoming a member of the main company in 1998. While at Second City Detroit he participated in the 1999 show "Phantom Menace to Society." Jackson moved to Los Angeles in 2001. He taught improv at Second City Hollywood. The 313 is named for Detroit's area code and is made up of mostly former Detroit residents, including
Keegan-Michael Key,
Larry Joe Campbell, Joshua Funk, Nyima Funk, Andy Cobb,
Maribeth Monroe, and Jaime Moyer. The 313 continues to perform at comedy festivals around the country, including
Las Vegas, After meeting Mark Gagliardi and Ben Acker at Second City Hollywood, Jackson was invited to one of the first rehearsals of what would become the
Thrilling Adventure Hour and became a member of the
WorkJuice Players, playing Sparks Nevada in the regular segment "
Sparks Nevada, Marshal on Mars". The show has been running as a live stage show since 2005 and has been published as a podcast since January 2011. Jackson also appeared in the film
Drones, which was written by Acker and Blacker and directed by
Amber Benson and
Adam Busch. Jackson is one half of a double act with comedian Carrie Clifford in which they play Sky & Nancy Collins, characters who live in Orange County and are trying stand-up for the first time because their friends find them funny. They have appeared on
Last Comic Standing, on
Last Call with Carson Daly, and at the
Hollywood Improv.
Acting Jackson starred in a web series in 2011 directed by
Jordan Vogt-Roberts called
Fox Compton. He has gone on to work with Vogt-Roberts many times, including on the film
The Kings of Summer in 2013,
Kong: Skull Island in 2017 and in the television series
Mash Up on
Comedy Central. Jackson has made guest appearances in a number of other television series, including
Key & Peele,
Psych,
Arrested Development,
Happy Endings,
The Middle,
2 Broke Girls,
Modern Family,
Kroll Show,
Hello Ladies, and
Black-ish. In 2012, Jackson starred in
Suit Up, a web series co-produced by
DirecTV and
Fox Digital Studio, as Jim Dunnigan.
Suit Up was the first of Fox Digital Studio's series to be picked up for a second season. In January 2012, Jackson stood in for
Bradley Cooper to play the part of Ben in a staged reunion performance of
Wet Hot American Summer at the
San Francisco Comedy Festival. Jackson appeared as attorney Trevor Nelsson in 10 episodes of
Michael Schur's comedy series
Parks and Recreation. From 2013 to 2021 he played Kevin Cozner, the husband of Captain Raymond Holt, played by
Andre Braugher, in Schur and
Dan Goor's series
Brooklyn Nine-Nine. He continued his affiliation with Schur in
The Good Place as Shawn, who is first identified as the judge of conflicts between the Good Place and the Bad Place, but is later revealed to be a supervisor of the Bad Place. Jackson hosted
The Good Place: The Podcast and
Brooklyn Nine-Nine: The Podcast for NBC. Jackson had a supporting role in the Amazon pilot
The Rebels, which premiered online in 2014 but was not picked up for a full series. In February 2014, it was announced that Jackson would play the role of Jim in the Fox pilot titled
Fatrick, along with
Marcia Cross. The pilot was not picked-up as a series.
Voice work Jackson is known for his voiceover work, which includes movies like
President Wolfman, radio series such as
Adventures in Odyssey and web series including ''
Funny or Die Presents: Brick Novax's Diary''. In October 2013, Jackson appeared as Marcus Vanston in a live performance of the podcast
Welcome to Night Vale. This episode, titled "
The Debate", was released on May 1, 2014.
Advertising Jackson has appeared in numerous national ad campaigns, including Farmers Insurance with
J.K. Simmons, Sears, Coors, Aaron's, Progressive, DirecTV and AT&T. == Personal life ==