Ben Affleck, 2002
Sure, Ben had shown us that he had romantic leading-man material in Pearl Harbor prior to snagging the sexiest title in 2002. And sure, he had a busy year starring in The Third Wheel, The Sum of All Fears, and Changing Lanes. But we all know what put him over the edge that year: Ben started dating Jennifer Lopez in 2002 while filming Gigli, and they got engaged the same year. Too bad the highly publicized and short-lived relationship would go down in breakup — and nickname — history.