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The casting of Battlestar Galactica's Tricia Helfer in "Roadkill" stemmed from the producers' preference to hire actors important to Supernatural's fanbase. This was the first episode to have the Winchesters as supporting characters, and Kripke felt "Tricia had the charisma to perform the leading role". Kripke enjoyed Emmanuelle Vaugier's work in television series such as Smallville, and believed she was an "easy choice" for the large role of the soon-to-be werewolf Madison in "Heart". Director Kim Manners felt Vaugier brought to the character a vulnerability like that of Lon Chaney, Jr. in The Wolf Man, which made viewers sympathetic. Conspiracy-theorist Ronald of "Nightshifters" was envisioned by writer and consulting producer Ben Edlund as the unsympathetic "semi-drunk Randy Quaid from Independence Day". However, this changed with Chris Gauthier's casting, and Edlund felt that Ronald turned out to be a "really cool" character fans would enjoy. The producers considered Summer Glau for the role of the zombie Angela for "Children Shouldn't Play with Dead Things", but she could not accept due to scheduling conflicts.

Many factors went into the casting decisions of the season's guest stars. Linda Blair, famous for her role in the horror film The Exorcist, appeared in the episode "The Usual Suspects". Though a fan of the show, Blair had turned down a guest appearance in the first season because she did not want to return to horror, having spent years getting a "clean slate". This changed after the television series Extra aired a three-part profile on her acting career and work with animals. It attempted to find a series that would write a role for her as "an actor's piece", rather than a cameo. Kripke, a fan of The Exorcist, offered to write an episode specifically for her, and she was "really touched" when he listened to her request to leave out demons in the storyline. During automated dialogue replacement, Jensen Ackles added in a reference to The Exorcist with the statement, "I could really go for some pea soup." Other characters returned from the first year. Actor Jim Beaver made multiple appearances as hunter Bobby Singer, an old family friend of the Winchesters. Beaver had expected his first-season guest appearance to be a "one-shot deal", and was surprised when he was asked to return. Adrianne Palicki reprised her role as Sam's deceased girlfriend Jessica in the alternate-reality episode "What Is and What Should Never Be", as did Samantha Smith as Mary Winchester. Smith also made an appearance in a flashback in the penultimate episode, "All Hell Breaks Loose, Part One". And though at first reluctant because of his role on Grey's Anatomy, Jeffrey Dean Morgan returned as John Winchester in the season premiere and finale. However, the character dies in the premiere because the writers worried that having him separated from his sons again—Sam and Dean spend much of the first season tracking him down—would "split the show" by having him away "doing more interesting things than the boys are doing". As a demon, the villain Azazel periodically switches hosts, and was first fully portrayed by Morgan in the first-season finale. The reins passed to Fredric Lehne for the second-season premiere, and the show's producers enjoyed his performance so much they brought him back for the two-part finale.

The writers used the second season to expand upon the concept of hunters, resulting in the introduction of many recurring characters through the hunter-frequented saloon Harvelle's Roadhouse. Samantha Ferris portrayed Ellen Harvelle, proprietor of the Roadhouse and an old friend of John Winchester, while Alona Tal played Ellen's daughter Jo. This pair complemented the father-son relationship of the Winchesters in the first year. Ferris believes she was exactly what the producers were looking for: a "tough, strong, yet a little maternal actor". Tal's character, on the other hand, was an intended love interest for Dean, and was eventually phased out because she came off as more of a sister figure. Chad Lindberg portrayed the genius Ash, who uses his vast computer skills to track the paranormal. Because the writers felt the character's "comical" and "wacky" personality was too unrealistic for the show, he was also removed by the finale.

The season aired Thursdays, 9:00 pm ET in the United States, and was the first season to air on the CW television network, a joint venture of The WB and UPN. The previous season was broadcast on The WB. It averaged only about 3.14 million American viewers, and was in danger of not being renewed. The cast and crew garnered many award nominations, but the episodes received mixed reviews from critics. While both the brotherly chemistry between the lead actors and the decision to finish the main storyline were praised, the formulaic structure of the episodes was criticized.

Season two of Supernatural, an American paranormal drama television series created by Eric Kripke, premiered September 28, 2006, and concluded May 17, 2007, airing 22 episodes. The season focuses on protagonists Sam (Jared Padalecki) and Dean Winchester (Jensen Ackles) as they track down Azazel, the demon responsible for the deaths of their mother Mary and father John. They attempt to discover the demon's plan for Sam and other psychic children—young adults who were visited by Azazel as infants and given abilities, and whose mothers often then died in a fire. During their travels, they use their father's journal to help them carry on the family business—saving people and hunting supernatural creatures.

When production of the second season started, Kripke wanted to avoid the monster-of-the-week formula used in the first year. The writers attempted this by including more "human themes," mainly "the things Sam and Dean are truly afraid of: death, grief, betrayal, etc." This change brought the series' focus onto situations such as the brothers dealing with their father's death and giving them the task of hunting down Azazel, the demon who killed him. Morgan feels that the brothers' "inner turmoil" created by the death of his character made them more three-dimensional. While Dean has trouble dealing with his father's death, Kripke wishes they had focused more on Sam's reaction. Instead, the episodes dealt more with Sam's fear of becoming evil, which Kripke regretted since the writers never depicted the character committing malevolent acts. Another main storyline of the season followed Sam and Dean as they track down the various psychic children—young adults like Sam who were visited by Azazel as infants and given abilities. However, the psychic children storyline made the mythology of the second season "dense" and "confusing" for Kripke.