The groundbreaking directed was the first African-American and the youngest director ever nominated for Best Director, sorry Damian. Even more spectacualar, he was only 24 years old and his film, Boyz n the Hood was his first ever feature film. The movie which if you haven't seen it, change that now was a story about the different pathways young black men in South Central Los Angeles. The movie was partly inspired by Singleton's life. To get cultured for the culture, check out some interviews Singleton did about his seminal work.
He was the director and screenwriter.
Even more phenomenal - the script was originally intended to be part of a film school application but eventually was sold to Columbia Pictures when graduating when he was 22. Originally Hollywoo didn't want him to direct the film to which he objected. More than likely they'd probably look at some white directors if Spike Lee was busy. No one was going to tell his story the way it is meant to be told.
Like his first film had a whole ass stellar cast too - Regina King, Ice Cube, Laurence Fishburne (what's in your wallet?), Ice Cube, Film Institution Angela Bassett, Morris Chestnut, etc.
The film granted critical acclaim and the awards soon followed, but Singleton made history twice being the first black and the youngest director ever nominated. The film was also nominated for Best Original Screenplay. Yes, playa ain't no Amistad give us free here. Yes, OP know there's are issues with the fact that a majority white male institution should not be the scale on which we measure success, but damn it, it's just nice to see a young black man get recognized for his work and for non mediocre work and there wasn't no slave film.
He didn't win that went to another directing legend, Jonathan Demme, for Silence of the Lambs, but we out here! Singleton, ever the humble, seemed quite stoked that Demme won.
Sources 1 2 3
RIP to this OG - he put his foot in this film and his legacy includes boosting up so many black creatives. Note: OP couldn't find any red carpet clips on him at the 1992 Oscars and like a five second clip of him actually there, so it's best to just hear those moments from the man himself and the people with whom he worked.