He played Richard Splett on the HBO political comedy series Veep, first appearing in four episodes during season 3 as the handler for Selina Meyer during her Iowa book tour.

[17] He has also appeared in films including We're the Millers, Horrible Bosses 2, Spy,[14] Neighbors 2: Sorority Rising, Mike and Dave Need Wedding Dates, and Ghostbusters.

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.

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 2021, Richardson appeared in Ted Lasso as Edwin Akufo, a part for which he was nominated for the Emmy for Outstanding Guest Actor in a Comedy Series in 2022 and 2023.