Richard Dale Jenkins was born in DeKalb, Illinois. At Wesleyan University he earned a degree in dramatic art; after that he continued his education at Indiana State College. It was there that he met the widely known acting teacher Harold Guskin; communication with him helped Jenkins greatly improve his professional skills. From that moment Richard's acting career began – he worked long and successfully in various local theaters, in particular at the Trinity Repertory Theater in Rhode Island (the actor spent about thirty years there and also managed to work as a director). In the mid-seventies Jenkins began getting roles in film and television; it started with the PBS broadcast of the Trinity Repertory Theater production 'Feasting With Panthers', which told of the imprisonment of the legendary playwright Oscar Wilde. The following year Richard and his family moved to Los Angeles for a while to try himself on the big and small screen; he did not like it, and after ten months he returned.

In the early eighties his television and film career began to develop little by little; particularly noteworthy is his role as the husband of Veronica Cartwright in 'The Witches of Eastwick' and a whole set of policemen, special agents and other extremely dangerous characters in 'Little Nikita', 'Sea of Love' and the TV film 'Challenger'. After about ten years of various dramatic roles, Jenkins finally attracted the attention of a wide audience by appearing in David Russell's comedy 'Flirting With Disaster' with Ben Stiller, Patricia Arquette, Lily Tomlin, Alan Alda and George Segal. Richard's staid appearance contrasted so much with the behavior of his character that the public was simply struck; comedic roles poured onto the actor as if from a horn of plenty. The Farrelly brothers made use of Jenkins' services, casting him first in 'There's Something About Mary', and then in the comedy with Jim Carrey 'Me, Myself and Irene' and in the film with Heather Graham 'Say It Isn't So'.

No less successfully Jenkins worked with another cinematic duo of brothers – Joel and Ethan Coen. The brothers first learned about Richard when he auditioned for the role of William Macy in 'Fargo'; they still did not cast him in their film. The situation changed in 2001, when Jenkins did appear in the neo-noir 'The Man Who Wasn't There'; his character was a heavily drinking lawyer and the father of a femme fatale played by Scarlett Johansson. Two years later Richard played a far more sober character in 'Intolerable Cruelty', and in 2008 he again came to the Coens, playing a gym manager in the black comedy 'Burn After Reading'; in that film a former CIA agent lost his memoirs in his gym, and two subordinates of Richard's character, played by Brad Pitt and Frances McDormand, tried to profit from it.

At present the actor is one of the busiest performers in the world and manages to masterfully combine work in theater, film and television.