Jack Ruby Shoots Lee Harvey Oswald is a 1963 photograph of nightclub owner Jack Ruby shooting accused assassin Lee Harvey Oswald. The image was captured by Dallas Times Herald photographer Robert H. Jackson and it won the 1964 Pulitzer Prize for Photography. Jackson began working for the Dallas Times Herald in 1960.
Jackson captured the image in the basement of the Dallas jail at the exact moment when Lee Harvey Oswald was shot. Another reporter, Jack Beers of The Dallas Morning News, captured a similar photo; but he clicked the shutter slightly before Ruby fired the shot.
In addition to the Pulitzer Prize, the Jackson image also won awards from the Texas Headliners Club and Sigma Delta Chi. In 2019 The New York Times said the image was "chillingly captured".