- May 1 Janet Pilgrim, American early playmate model for Playboy (July 1955, Dec 1955, Oct 1956), dies at 82
- May 2 Vincent Baggetta, American actor (Lou-Chicago Story), dies at 72
- May 3 Daliah Lavi [Levinbuck], Israeli actress (Casino Royale: Lord Jim), and singer, dies at 74
- May 3 Lukas Ammann, Swiss actor (Graf Yoster; Day of Anger; Class Reunion; Palace Hotel), dies of complications from surgery at 104
- May 9 Michael Parks, American actor (Tusk, Then Came Bronson), dies at 77
- May 10 Geoffrey Bayldon, British stage and screen actor (Catweazle; Worzel Gummidge - "Crowman"), dies at 93
- May 14 Brad Grey, American film and TV producer (Sopranos), Chairman of Paramount Pictures, dies of cancer at 59
- May 14 Powers Boothe, American Actor (Sin City, Deadwood), dies at 68
- May 18 Roger Ailes, American TV executive and CEO of Fox News (1996-2016), dies at 77
- May 20 Jimmy Dale, British-Canadian pianist and orchestra leader (The Sonny & Cher Comedy Hour), dies at 81
- May 22 Dina Merrill, American actress (Operation Petticoat, Butterfield 8), dies at 93