A movie about the wine industry and fraud, Sour Grapes: https://www.rottentomatoes.com/m/sour_grapes_2016/

If you want to do long dives anything by Ken Burns, baseball is a classic: http://www.pbs.org/kenburns/baseball/

A documentary about Napster directed by not Keanu of Bill and Ted's Excellent adventure, Downloaded: https://www.imdb.com/title/tt2033981/