Making a film on the life of J. Edgar Hoover is no easy feat. Despite being of the most powerful men of the 20th Century, there is much about Hoover that is unknown, ranging from his sexual orientation to the secrets he held on public officials. Clint Eastwood tackles this ambitious project with J. Edgar, and unfortunately, he fails to meet the challenge. J. Edgar is a long, meandering movie, that winds up being a wholly unsatisfying portrait of the former head of the FBI.

J. Edgar essentially follows two tracks. Much of the film is told from Hoover’s flashbacks as narrated to biographers and PR men in the 1960s.  The flashbacks begin with Hoover’s ascent to power around the time of the Palmer Raids and particular detail is given to the kidnapping of Charles Lindbergh’s child.  The film gives tremendous credit to Hoover for pushing advances in criminal science into an antiquated justice system. Hoover was among the first to advocate for finger printing and introducing forensics into the investigative process.

But the film also takes care to note Hoover’s shortcomings, including his irrational paranoia and jealousy that led to numerous abuses of power. It appears to take a stand that Hoover was a closeted homosexual for his entire adult life. And it portrays Hoover as a man obsessed with obtaining damming private information on public figures which he used to assert his power.

Leonardo DiCaprio stars as Hoover in a performance that was seemingly designed to win him an Oscar. It may very well earn him his fourth nomination (he was also nominated for Blood Diamond, The Aviator, and What’s Eating Gilbert Grape?), but this was not DiCaprio’s best work. Too much of the movie is spent with him playing an aging Hoover, and the performance is hardly believable. The makeup on DiCaprio seems almost cartoonish, and he really struggles to inhabit the body of a 60-plus year old man. The voice of a 24-year old Hoover sounds exactly the same as the voice of a senior citizen Hoover, and it’s an overall disappointing effort. DiCaprio is quite good at portraying a younger fast-talking Hoover though.

The one standout performance comes from Armie Hammer, who plays Clyde Tolson, Hoover’s closest friend and right-hand man. The pair share a bizarre, but convincing homoerotic relationship throughout the film. Best-known for playing both Winklevoss twins in The Social Network, Hammer proves he has range in this very unique and challenging role – starting off as an obviously closeted rich homosexual law school grad and transitioning into an old broken-down unfulfilled stroked-out sidekick.

Naomi Watts deftly plays Helen Gandy, a career-minded woman who once refused Hoover’s marriage proposal, yet wound up being his personal secretary for his entire professional career. The complicated character manages to be stripped of Watts’ usual glow and sexual attractiveness, and comes across as both subservient and ambitious. Judi Dench does an admirable job playing Hoover’s domineering mother, a woman that Hoover lives with for most of his adult life. She’s always a treat to watch.

But the performances aren’t the real problem with J. Edgar. While Eastwood has directed some excellent movies in recent years (Million Dollar Baby, Gran Torino, Invictus, Letters from Iwo Jima), he’s also had his share of disappointments (Changeling, Hereafter). This falls into the latter category.

Eastwood glosses over some real potentially fascinating moments in history. There’s hardly any mention of World War II or McCarthyism. His relationships with presidents from Roosevelt to Kennedy are glossed over and never shown to satisfaction. His pursuit of mobsters is dealt with awkwardly and not shown in any depth. Furthermore, much of the film relies on Hoover’s flashbacks which are evidently inaccurate, so the viewer is never completely certain as to what the real version of historical events might be. Too much of the film takes place with an old reminiscing Hoover yammering about nonsense, when a more complete biopic would have taken equal looks at Hoover through time and dedicated a more proportional amount to his later years.

As noted at the top of this article, it is difficult to make a film about someone who was so mysterious, about whom many questions still exist. But Eastwood doesn’t answer many of the questions to a level of satisfaction. It’s understandable that J. Edgar doesn’t necessarily take a side on the complicated man, but it’s disappointing that the film doesn’t act with conviction either.

The end result of J. Edgar is a drag of a film that offers a few interesting looks at a complicated man, but ultimately doesn’t succeed at meeting its inherently ambitious goals.