Philip Seymour Hoffman gets my vote as one of the five greatest living movie actors. He recalls those golden days during the late 1960s and 1970s when actors like Gene Hackman and Dustin Hoffman were cast because of their personality and skill, rather than looks. He can do anything. He could play a romantic lead, he's a comedian, he can play passive and sad, as well as aggressive and dangerous. He could be a silent clown, or Philip Marlowe, or Othello. So I was excited to take on a "Their Best Role" for him. But it wasn't long before I was faced with his impressive filmography -- which looks a bit like someone's list of the best films of the decade -- and daunted by the prospect of choosing just one movie, one role. I decided to start in 1997, when Hoffman gave his breakthrough performance in Boogie Nights, and then proceed in a process of elimination.

First, I crossed off the flat-out horrible movies, like Patch Adams (1998) and Red Dragon (2002), though there weren't many. After that went the so-so movies that Hoffman managed to rise above, and stand out in, like Cold Mountain (2003), Along Came Polly (2004), Mission: Impossible III (2006), Charlie Wilson's War (2007) and Pirate Radio (2009). Next up, I took out the movies in which Hoffman's role wasn't necessarily one of the biggest or showiest, and wouldn't be called his "best role," even if the movies were good: Boogie Nights (1997), Next Stop Wonderland (1998), The Big Lebowski (1998) and The Talented Mr. Ripley (1999).

Then I stopped to think: "Geez. This guy has been in a ton of great movies," before I continued, this time cutting out movies that were good, but were somehow depressing and hard to watch. These were movies that I admired more than I liked: Happiness (1998), Love Liza (2002), Owning Mahowny (2003), The Savages (2007) and Synecdoche, New York (2008). Then I eliminated a pair of good, but lightweight movies, State and Main (2000) and Doubt (2008).

That brings us down to half a dozen final contenders. Let's take out Punch-Drunk Love (2002), which is a great film, but Hoffman's role in it is small and not particularly important to the whole. Next, we'll take out Before the Devil Knows You're Dead (2007); it's a film I loved and continue to treasure, but it seems more like an example of a classically well-made crime film than anything that might be called a film for the ages.

Now the tough one: Almost Famous (2000). Hoffman's Lester Bangs could very well qualify as his best role; he's lots of fun in this movie and has all of the best lines, but unlike most of the free world, I don't much care for the rest of the movie. I understand why most journalists like it -- because it's a fantasy story about journalism -- but half of the characters are flat, especially the passive lead character, and then there's Kate Hudson to deal with, and director Crowe's penchant for rambling on far too long. So it's out.

Next up, we'll tackle Hoffman's Oscar win, for Capote (2005). It's a great, great performance, no question, and it's a well-made film that manages to do something fresh with the tired old biopic formula. But as evidenced by Toby Jones' comparable performance in the following year's Infamous, Hoffman's wasn't the one and only, ultimate Capote. He did not make the part his own.

OK. Now we're down to the final two: English teacher Jacob Elinsky in Spike Lee's 25th Hour (2002) and nurse Phil Parma in Paul Thomas Anderson's Magnolia (1999). I like these two performances best because they seem to me to be the most revealing of Hoffman. They're the two saddest and most introspective. Hoffman watching over the dying Jason Robards in Magnolia offers him some truly powerful moments; he seems unprepared for the real world and facing it unexpectedly, all at once, in all its ugly glory. But if we consider the large, ensemble cast of that movie, Hoffman is really only a small cog in the machine, and he doesn't come off nearly as well as Tom Cruise, with the greatest role of his career.

So there it is. Hoffman's best role is Jacob Elinsky in 25th Hour. I was terribly, terribly moved by this tale of three friends going out on the town the night before Monty (Edward Norton) goes to prison. Director Lee steeped his movie in New York life and post-9/11 sorrow without directly referencing it or milking it for cheap glory. The three friends were as different as friends could be, but their bonds ran deep, and together they reminded me of my own, oldest friends. Hoffman's helpless relationship with his pretty student (Anna Paquin) is both thrilling and sad, and it gave his Jacob something to focus on other than his pal Monty; any other movie would have simply shown Monty and his "best friends" (all of whose lives revolve entirely around Monty) but 25th Hour bothered to give weight and history to the others as well.

What's more is that, though Hoffman is not the lead character, his contribution is essential to the film's final formula. He's weakness and romance, there to juxtapose the hardness and confidence and cynicism of the other characters. His costume is perfect: shabby schoolteacher tie and cheap coat (which he leaves on, even in a nightclub), glasses and a Yankees hat. Yet these attributes are so well-played that Jacob doesn't seem weak or pathetic. He just seems human. I met Hoffman twice over the years, and I liked him immensely, but I have to say that I feel I got to know Jacob far better than I got to know the real man. That's great acting, and it's the pinnacle (so far) of a truly great career.