Time does go by fast. I remember quite well seeing Boyz n the Hood when it came out in 1991; I saw it in a theater in Manhattan that has since been torn down. No need to go into how impressive a debut film that was by twenty-three year old director John Singleton or how that film's success shadowed the rest of his career. Make that strong a movie on your first try, and at such a young age, and people compare every film you do subsequently to that debut.
I liked Singleton as a director. Above all, I got the sense he tried to put as much of himself and his concerns as he could into every film he made, regardless of how personal the material was to him. And he certainly made crime, in one form or another, central to his work. He dealt with it in a serious and realistic fashion, like in Boyz n the Hood, and he could handle it in a more over the top popcorn entertainment kind of way, like in Four Brothers (a film I enjoy every time I see it, especially for Chiwetel Ejiofor's performance as the bad guy, Victor Sweet). On Shaft, there was contention on the set involving Singleton, Samuel Jackson, and Richard Price after the producer brought Price in to rework Singleton's script, but this is another film that, while no masterpiece, is fun to watch. And again Singleton showed his talent for casting great actors as his villains to help make the dramatic stakes high: in Shaft you've got both Christian Bale and Jeffrey Wright (as the wonderfully named Peoples Hernandez) as the nasty ones Shaft has to take down.
Overall, and though he makes some changes to the historical record, I think Rosewood is Singleton's most gutsy and ambitious film. I remember being amazed, when the film was released, that I had never even heard of the 1923 massacre in Florida, a case where a mob of whites, after a white woman accused a black man of assault, destroyed the primarily black town of Rosewood. Many town residents were killed and the town was all but burned to the ground. Rosewood is the film in which Singleton works on his largest scale, with a big cast, and asks people, in the most serious way, to grapple with American history at its ugliest. Perhaps unsurprisingly, it's not a film that did well at the box office, and Singleton never really tried to make a film that ambitious ever again. But it's well worth seeing if you haven't seen it yet, and it doesn't take much insight to say that it definitely remains a relevant film.
RIP John Singleton