This was a film that grew on me, as it started out very boring and became more interesting as time went on. Director/Cameraman Michael Almereyda starts by following Eggleston and his assistant/son Winston as they wander around Mayfield, Kentucky on a commission from Gus Van Sant to shoot photographs. Almereyda's hand-held camera shakes and picks up the wind and all sorts of extraneous noises while Eggleston barely says anything and when he does, it needs sub-titling to help you make it out. They then make their way home to Memphis, Tennessee and stop off at a ruined house for sale by the side of the road, which is advertised as a "real fixer-upper", and suddenly you start seeing the beauty of the things that Eggleston is seeing in the damaged green roof or the patterns of sunlight on the dusty floors. Soon you are at home with him where he does some amateur improvisations on his electronic keyboard and piano.
Then he takes you along on a trip to visit his girl-friend Leigh Haslip. Eggleston has been quite happily married to his wife Rosa for 40 years, and she must just humour his occasional philandering as she later describes him and his family as "He's sweet, all the Egglestons are sweet, it's in their genes". At Haslip's house, Eggleston sketches a free-form portrait while Haslip herself rather drunkenly rambles and lounges on a couch in her pajamas. Eggleston is still not saying a lot, but you are gradually liking him more and more, as you realize this is an artist with no pretensions whatsoever. He is what he is and he does what he does and he doesn't care about having to explain himself or his work to you at all. You can take it or leave it.
For the rest of the film you follow along on a few more trips such as to the Getty Museum in LA where Eggleston walks around rather anonymously at his own photographic exhibit. You get to view a few clips from Eggleston's own black and white experimental video film "Stranded in Canton" (1973/74 - completed 2005). There is a single scene towards the end where Almereyda finally tries to get Eggleston pinned down to talk art and photography with provocations such as "real life is an illusion. photographs are the reality", but Eggleston protests and disagrees and says that he doesn't understand what Almereyda is talking about. So you never get any answers or explanations from Eggleston himself.
When the credits role at the end with the sound of Roy Orbison's beautiful singing of the song "In the Real World" you are back again at Leigh Haslip's house where both she and Eggleston are gleefully enjoying the song on the stereo while they talk about how happy they are to have not been born in the Middle Ages before there was Roy Orbison. And I'm just as happy to have not been born before there were the photographs of William Eggleston and this film by Michael Almereyda.