[1] In 2001 and in 2005, he received three awards for best arts criticism from the Association of Alternative Newsweeklies.
In 2005, he began shooting a documentary named Moving Midway, which shows the effect on his family of the moving of the family's plantation house from a site near a busy road back into the woods and a proper, tranquil setting, and at the same time, the effect on his family of meeting descendants of slaves his family had owned, including those descended from a slave and his great-grandfather.
[1] At that time he began writing film criticism professionally.
Of special interest to him are cinematic representations of the Southern United States, Iranian film, and the transition from analog to digital technology.
[1] Cheshire participated in the 2012 Sight & Sound critics' poll, where he listed his ten favorite films as follows: 2001: A Space Odyssey, Ali: Fear Eats the Soul, Battleship Potemkin, Close-Up, The Godfather: Part II, Intolerance, A Man Escaped, The Man Who Shot Liberty Valance, The Passion of Joan of Arc, and Rear Window.