24. 'J. Edgar' (2011)
Clint Eastwood's long, lumbering, awkward biopic about the man who changed the face of American surveillance asks a lot of Leo – he has to age decades, he has to make a monster likable, he has to depict forbidden, and barely repressed passions. But the movie itself doesn't really give him the support he needs, and the script alternates between the obvious and the inert. Although DiCaprio gives it his best, the film mostly leaves him flailing. That said, the chemistry between DiCaprio and co-star Armie Hammer, playing J. Edgar Hoover's longtime love interest and companion, is occasionally quite compelling.