Smilin' Jack or Smiling Jack may refer to:
The Adventures of Smilin' Jack, an American newspaper cartoon strip that ran from 1933 to 1973 The Adventures of Smilin' Jack (serial), a film serial based on the cartoon strip Smilin' Jack Smith (1913–2006), an American singer, radio host, and actor John M. Conroy (1920–1979), an American actor, aviator, and businessman, nicknamed "Smiling Jack" John Tait (runner) (1888–1971), a Canadian athlete John F. Wiley (1920–2013), an American football player and coach, nicknamed "Smiling Jack"
See also Happy Jack (disambiguation)