Road to Perdition (2002) is still one of the more intriguing gangster movies I've seen, mostly because its real interest is the human side, which in these films usually means you're a Corleone trying to survive attrition. Well, this time the name is Sullivan and of all people it's Tom Hanks in the lead role, and his godfather is Paul Newman. Both are excellent in the film, as are Jude Law and Daniel Craig (if it seems like Craig is in a lot of my selections, it's coincidental except for Quantum of Solace; otherwise it's a testament to his versatility and overall skill). From director Sam Mendes and featuring some of the best cinematography you're likely to ever see in film, Road to Perdition is a gem that could use a little more exposure.
Star Trek bonus!
R is for Riker, William T.
(from Star Trek: The Next Generation)
The first officer who was repeatedly offered his own command but chose to stick with his family (even though he and Deanna Troi had some pretty bad commitment issues), Riker is one of the reasons Picard's crew and Next Generation ultimately proved such a worthy follow-up to the original series. For one thing, he was in many ways a reincarnation of Kirk, and yet never came off as a carbon copy. If anything, his studied cool in most situations helped set the tone of his series almost as much as his captain. Jonathan Frakes went on to direct his castmates in two of their movies, including the excellent First Contact, and appeared in all three subsequent TV shows in one incarnation or another. This guy, in fictional and real-life form, is arguably the MVP of the modern set.