At age twenty-four, Kirkland was hired as a staff photographer for Look magazine and became famous for his 1961 photos of Marilyn Monroe taken for Look's 25th anniversary issue. He later joined the staff of Life magazine. Notable persons have posed for Kirkland from the great photography innovator Man Ray and photographer/painter Jacques Henri Lartigue to Dr. Stephen Hawking. Entertainment celebrities he has photographed include Mick Jagger, Morgan Freeman, Orson Welles, Andy Warhol, Coco Chanel, Marlene Dietrich, Brigitte Bardot, Judy Garland, Elizabeth Taylor, Sophia Loren and Catherine Deneuve. Kirkland's portrait of Charlie Chaplin is at the National Portrait Gallery in London.