He has also appeared on television, and won a Primetime Emmy Award for Outstanding Individual Achievement for his performance in the 1982 NBC broadcast of Ain't Misbehavin'.

He performed in a number of Off-Off-Broadway productions at La MaMa Experimental Theatre Club in the East Village of Manhattan during the 1970s, 1980s, and early 1990s.

These included Ken Rubenstein's Sacred Guard (1973),[2] Lamar Alford's Thoughts (1974),[3] and the Cotton Club Gala with music by Aaron Bell and directed by Ellen Stewart (1985).

[13] In 2000, De Shields originated the role of Noah "Horse" T. Simmons in the Terrence McNally / David Yazbek musical adaptation of the film The Full Monty.

De Shields' regional theatre credits include Play On!, The Full Monty, Waiting For Godot, The Man Who Came to Dinner, Death of a Salesman, Dusyanta: A Tale of Kalidasa, The Gospel According to James, Camino Real and King Lear.

De Shields, Lillias White, Stefanie Powers, and Georgia Engel starred in the new musical Gotta Dance, directed and choreographed by Jerry Mitchell.

On January 26, 2021, it was announced that De Shields would reprise his role as Hermes in Live From Mount Olympus, a narrative podcast for tweens directed by Rachel Chavkin and Zhailon Levingston.

De Shields' co-stars include fellow Hadestown cast member Amber Gray, Divine Garland, Vinie Burrows, Kristen Sieh, and more.

He won an Primetime Emmy Award for Outstanding Individual Achievement for his performance in the 1982 NBC broadcast of Ain't Misbehavin', and played Tweedledum in a 1983 televised production of Alice in Wonderland that also featured Eve Arden, Richard Burton, Colleen Dewhurst, James Coco, Kaye Ballard, and Nathan Lane.

On December 28, 2020, it was announced that De Shields would star as Anton Ego in a benefit concert presentation of Ratatouille the Musical, an internet meme that originated on TikTok, inspired by the 2007 Disney/Pixar film.

BOOM!, released on Netflix on November 12, 2021, as a patron of the Moondance Diner in the musical scene for "Sunday", as well as other Broadway actors such as Chita Rivera, Renée Elise Goldsberry, Phillipa Soo, among others.

[24] In March 2024, De Shields was announced to be portraying Old Deuteronomy in Cats at the Perelman Performing Arts Center in the summer of that year.

[25] He's set to reprise his role as Hermes in the West End production of Hadestown opposite original Broadway cast stars Carney, Noblezada, Gray and Page for a limited engagement from February to March 2025.