Sweet, sexy and boyishly goofy, this tall everyman unwittingly began laying the groundwork for an entertainment career while still in high school, when he appeared in a play penned by his classmate B.J. Novak. About a decade later, Krasinski got his big break playing a lovesick worker on another Novak project, the Emmy-winning sitcom The Office. Krasinski initially pursued writing, graduating from college as an honors playwright and working as a script intern for Late Night with Conan O'Brien. In the '00s, he added a number of small, blink-and-you-missed-them roles to his résumé before going to work at The Office.