He is best known for his appearances in a variety of horror films, including Cube, Wrong Turn, The Witch, Beau is Afraid, Ejecta, and Anything for Jackson, as well as for portraying Death in the dark fantasy series Supernatural.

In the 1996 film Hard Core Logo, he played the bitter, aging, punk rock legend Bucky Haight.

Richings performed in heavy makeup as cannibal-killer Three Finger in Wrong Turn (2003), and was a series regulars as the nearly-blind security guard Otto in Stephen King's 2004 miniseries Kingdom Hospital.

In 2006, he appeared in a brief speaking role as the Mutant Theatre Organiser in X-Men: The Last Stand, and played a vampire killer alongside in the direct-to-DVD horror film The Last Sect.

Richings made an appearance in the 2010 fantasy film adaption Percy Jackson & the Olympians: The Lighting Thief as Charon, the ferryman of Hades.

[18][19] In 2022, Richings appeared in the television shows The Umbrella Academy, Reginald the Vampire, and Guillermo del Toro's Cabinet of Curiosities.