Olyphant had a recurring guest role, as a fictionalized version of himself, in the Fox comedy "The Grinder" (2015–2016). His performance received positive critical notices, with "USA Today"s Robert Bianco declaring it an "Emmy-deserving performance." He won the Critics' Choice Television Award for Best Guest Performer in a Comedy Series. In early 2016, Olyphant starred in the world premiere of Kenneth Lonergan's comedy "Hold On to Me Darling" at the off-Broadway Atlantic Theater Company. His character, Strings McCrane, is a self-absorbed country singer and actor who returns to Tennessee, after his mother's death. Ben Brantley of the "New York Times" found him "entertainingly irritating" in a performance that "avoids the obvious route of histrionic posing": "The startling, bona fide sorrow that Mr. Olyphant brings to final scene truly illuminates everything that has come before." Frank Rizzo of "Variety" felt his performance was "a stunner, striking just the right notes of guilelessness, obliviousness and narcissism to make Strings one of the most appealing messes in a long time." David Rooney of "The Hollywood Reporter" felt the role "seems tailor-made for his laid-back swagger and sly humor ... Olyphant's natural charm ensures that Strings' unapologetic self-absorption remains more human than monstrous." He also played Henry, the ex-husband of Sandy (Jennifer Aniston), in the universally panned ensemble romantic comedy "Mother's Day" (2016) and appeared in Oliver Stone's "Snowden", as a CIA agent who befriended Snowden prior to the latter's departure to Russia after his leak of classified documents.