Early in his career, Richardson performed at the
Second City in Detroit and then in
Chicago. Following a move to
Los Angeles, Richardson appeared in six episodes (including the series finale) of
The Office and a season 4 episode of
Arrested Development. During season 4, Richardson was made a regular cast member of the show, after his character received a job offer in President Meyer's administration as an assistant to the character Jonah. He has also appeared in films including ''
We're the Millers, Horrible Bosses 2, Spy'', In 2015,
Comedy Central ordered a pilot for the series
Detroiters, created by Richardson and
Tim Robinson. The show stars Richardson and Robinson, who also co-wrote and co-executive produced the series with others. Comedy Central then ordered ten episodes of the series, which began shooting in the Detroit area in 2016. According to
Detroit Free Press, "In the series, Richardson and Robinson play struggling advertising men in Detroit who make local TV commercials. The plot was inspired partly by the classic Detroit ads they grew up watching, including the
Mel Farr Superstar and Gordy from
ABC Warehouse campaigns."
Detroiters ran for two seasons before its cancellation by Comedy Central in 2018. In 2016, Richardson was nominated for the Best Performance in a Variety or Sketch Comedy Program or Series (Individual or Ensemble) award at the
Canadian Screen Awards for his work on
The Second City Project. He was also nominated for the
Outstanding Performance by an Ensemble in a Comedy Series at the 2015, 2016, 2017, and 2018
Screen Actors Guild Awards for his work on
Veep, winning the last one. In 2018, he began playing Alf in the
YouTube Premium series
Champaign ILL. Since 2019, he has played various characters in the
Netflix sketch show
I Think You Should Leave with Tim Robinson. In 2022, Richardson appeared in the first U.S. advertising campaign for
Midea, a
Fortune Global 500 appliances company. The humorous campaign featured Richardson as a fictional
Chief Idea Officer who takes credit for Midea products, calling them "My Ideas" and claiming to be "the man behind the best ideas, at the world's best appliance company." In 2022, Richardson was in the main cast of the
Apple TV+ mystery comedy series
The Afterparty. That same year he appeared as Gilbert, the owner of the Olde Salem Magic Shoppe, in
Hocus Pocus 2, a sequel to the 1993 film,
Hocus Pocus. ==Filmography==