Timothy Olyphant Played Himself On This Short-Lived Rob Lowe Sitcom

Timothy Olyphant, best known for his roles as Raylan Givens in Justified and Seth Bullock in Deadwood, played a different kind of character in 2015. He joined Fox's sitcom The Grinder, a one-season series that ran from 2015 to 2016. The show starred Rob Lowe as Dean Sanderson Jr., a lawyer from a long-running courtroom drama also named The Grinder, who believed his TV experience made him qualified to practice law at his family's real law firm.

Olyphant played an exaggerated version of himself in four episodes, portraying Rake Grinder, the brother of Dean's character, Mitch Grinder, and creating a rivalry between the two. During an appearance on Conan, Olyphant joked about the preparation required to play himself, stating that he had been researching the role for years.

He also mentioned that this character was particularly challenging to detach from after work hours. Olyphant's performance earned him a Critics' Choice Television Award for Best Guest Actor/Actress in a Comedy Series in 2016. He joked on Conan that unlike other characters, this one stayed with him even after leaving the set. The fictional Olyphant's romantic storyline with Claire (Natalie Morales), an attorney at the Sanderson family's law firm and Dean's romantic interest, also caused complications.

He had to ask his real-life wife if it was okay to play an affair in the show, confident that she would say it was fine, and she did.