[2][3] He graduated from Amherst Central High School in 1988, and obtained a bachelor's degree from Calvin College in 1992 with a major in philosophy and minors in political science and environmental studies.

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.

[21] 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.

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.

[25] In February 2014, it was announced that Jackson would play the role of Jim in the Fox pilot titled Fatrick, along with Marcia Cross.

[32] Jackson has appeared in numerous national ad campaigns, including Farmers Insurance with J. K. Simmons,[33] Sears, Coors, Aaron's, Progressive, DirecTV and AT&T.

[39][40][41] The Project, which was inspired by a statement by Detroit mayor Dave Bing, was founded after a series of cookouts held at Jackson and Hagenlocker's home with other actors, writers, and directors who had connections to the city.