Some guest actors have said that the working environment on the show was very different from other shows, because the writers were really open to suggestions from the cast, even while shooting scenes, to the point of stopping shooting for a while and sitting around to discuss the scene if there was room for improvement.
Jeremy Davies (Dickie Bennett) was a fan of the show in its first season and asked to be considered for a role on the show. His performance as Dickie Bennett earned him back-to-back Emmy nominations for Outstanding Guest Actor in a Drama Series in 2011 and 2012, winning the award in 2012.
Throughout the series, the characters frequently drank Kentucky bourbon, particularly the top-shelf brand Blanton's. The Props Department poured the liquor out of the bottles, and replaced it with watered-down Diet Coke for the cast members to drink instead. Timothy Olyphant took the real bourbon home in mason jars. On the night the series finale aired, he brought a jar of bourbon on Conan (2010) to toast to the show with Conan O'Brien.
The character of Mags Bennett (Margo Martindale) was based on a a male character, Pervis "Speed" Crowe, the "marijuana king of East Kentucky," who featured in the Elmore Leonard novel "Raylan" (2012). Mags Bennett is instead the widow of Pervis Bennett. She is also partially based on a real-life criminal matriarch, Mags Bailey, who reportedly kept her money hidden under a black church. Martindale won her first Emmy Award for her portrayal of Mags Bennett, for Outstanding Guest Actress in a Drama Series.
The pilot was filmed in Pennsylvania. The rest of the series was filmed in Los Angeles County, California, most notably the Melody Ranch in Santa Clarita.