Jeffrey Wright did not receive an Oscar nomination for portraying Winston in Broken Flowers.
Jeffrey Wright is one of those actors who is always already giving very interesting performances, yet always flies under the radar for one reason or another, though that may be changing at least at the TV level due to his outstanding work Westworld, but I digress. Wright here plays the neighbor and friend to Bill Murray's Don. His character is a very amateur detective who loves crime fiction, and who takes a particular interest in the letter sent to Murray's character. The character is technically here to serve the purpose of sending Murray on his mission of sorts, and he in turns bookends the film with his "investigation". In perhaps the style of director Jim Jarmusch no one can simply serve just a purpose there always has to be more than that, there is certainly more than that to be had with Winston particularly with Wright in the role. Wright is a delight, and hey that rhymes but don't pay too much attention that statement. The point is though that Wright certainly makes Winston quite a character to say the least, which is not saying enough in this case.
Wright plays the part with a somewhat overt, though I wouldn't quite say broad accent, that already fills Winston with an abundance of color from the outset. Wright absolutely makes this accent his own and just adds to the very idea of Winston is this somewhat kooky neighbor. Wright plays the part as one almost completely comedic side of this dramatic comedy, most of the other major characters are filled with more than a little pathos in one way or another, offers the right presence with that in mind. There's a real sense of fun that Wright brings as he shows so much honest enthusiasm in Winston going about the task of investigating the letter and cracking the case. I love just how brightly optimistic Wright is throughout his performance that plays off Murray's dour style so well. Wright is quite amusing because of just how earnest he makes Winston in every moment as he dissects the case for Don, as though he really is in the middle of a truly important situation. This is all with this unabashed sweetness to Wright's work that presents Winston as a friend who only wants to help his friend, even if he perhaps gets too much joy out of the investigation itself. He's especially effective in realizing that in a moment near the end of the film, as Wright infuses such genuine concern as he apologizes for the problems he inadvertently causes. Wright isn't in the film all that much, though I enjoyed every minute he appeared and missed him when we left him. This is a role that could have been easily overblown but Wright finds just the right approach to make Winston only ever one endearing screwball.