Cowboy Bob may refer to:
People Bob Bradley (wrestler) (also "Cowboy" Bob Bradley; born 1958), American professional wrestler Bob Kelly (wrestler) (also "Cowboy" Bob Kelly; 1936–2014), American professional wrestler and booker Robert H. Macy (also "Cowboy Bob"; 1930–2011), American Democratic District Attorney in Oklahoma Bob Orton Jr. (also "Cowboy" Bob Orton; born 1950), American professional wrestler Peggy Jo Tallas (1944–2005), American bank robber nicknamed "Cowboy Bob" by the media
Fictional characters Cowboy Bob, from the daily syndicated newspaper comic strip Dennis the Menace Cowboy Bob, from the 1990 Simpsons episode "The Call of the Simpsons", voiced by Albert Brooks