101 Funniest Screenplays

The screenplay, by Alexander Payne and Jim Taylor, based on the novel by Rex Pickett, won an Oscar and Writers Guild Award. You could call Sideways a road comedy – the roads here being the ones that wind through Santa Barbara wine country, as a groom and his best man indulge in Pinot Noirs, Cab Francs, and a bit too much of the local flavor. In some ways, Paul Giamatti as the sad sack Miles, a frustrated novelist, and Thomas Hayden Church as the soon-to-be-married actor-hellcat Jack, have the makings of a classic comedy team. On their adventures, Miles is a straight man and Jack is the id-exorcising clown. But Payne’s and Taylor’s comedy, particularly after their more overtly satirical Citizen Ruth and Election, has come from exploring believably wounded men reconciling what it means to be male, and the bemusing gulf between their hopes and how their lives have actually played out.