Good Grief is a unique take on the plight of the supreme loser. Its protagonist, Chuck (David Gray), is a high school senior who lives for a Dungeons and Dragons-type game called Monsters and Mayhem. His friends are growing out of the game, however, and Chuck deals with their maturation through a fantasy world of chain mail, dragons, and hit points. Gray plays the serious, pent-up geek well enough that you will sympathize with him and laugh at his ability to say lines like "I already had my 'just desserts,' thanks" with a straight face.
Though certain aspects of the script don't delve deeply enough, the premise behind Dickson's story is fresh, translating the characters' conflicts into the sad, nerdy world of Monsters and Mayhem (made funnier by a contemporary hair metal soundtrack, including The Fucking Champs). The dialogue is believable, especially when lines are subtly ironic.
With its geeky feel and shots of familiar places--Belmont Street, the Stage 4 (now Meow Meow)--the film is distinctly Portland. If you can ignore sometimes-painful acting and a few plot holes, Good Grief is a well-directed, post-ironic, feel-good movie. It also hints at the talent that Dickson and cinematographer/mainstay Matt McCormick will hone with time.