Sam and Dean Winchester’s journey continued in Supernatural Season 2, meeting many more colourful characters along the way. Here are some of the most memorable for Courageous Nerd.
The Story Continues: Season 2
Following *spoiler alert*, the death of their father John (Jeffrey Dean Morgan) in the season premiere, Sam and Dean Winchester are now truly alone.
Supernatural Season 2 premiered in September 2006 and ended in May 2007.
Despite John’s death, Sam and Dean continue the “family business” and take down several demonic creatures. Along the way, they meet a variety of other characters. Some are good, some are very, very bad.
Following his introduction in the Season 1 finale, Bobby (Jim Beaver) becomes a recurring character in this season and beyond.
Across the 22 episodes of Season 2, the boys have plenty more adventures. This journey is still only in its early stages, after all.
“This demon killed your mother, killed your girlfriend! You begged me to be a part of this hunt! Now, if you’d killed the damn thing when you had the chance, none of this would’ve happened!”John Winchester, Season 2 Episode 1,
Honourable Mention: Regan Burns as”McG” in “Hollywood Babylon”, named after the real-life producer/director.
Episode: “Hollywood Babylon” (2×18)
Gary Cole has appeared in a wide variety of projects throughout his four-decade career. Some of his notable television work includes Veep, The Good Wife, The West Wing and Entourage. He has also had voice roles on Family Guy and Kim Possible.
Meanwhile, Cole’s films include Office Space, Dodgeball: A True Underdog Story and Talladega Nights: The Ballad of Ricky Bobby, to name a few.
In the Supernatural episode, “Hollywood Babylon”, Cole played “Brad Redding”, the producer of the (fictitious) movie Hell Raiser II.
Episode: “The Usual Suspects” (2×07)
A ‘scream queen’ and horror icon, Linda Blair is best known for playing “Regan MacNeil” in The Exorcist. Only 13 years of age at the time, Blair won a Golden Globe for her performance, in addition to an Academy Award nomination.
Four years later, Blair would reprise her role in the sequel; Exorcist II: The Heretic. She also made a brief cameo in Scream (1996) as a reporter harassing protagonist Sidney Prescott (Neve Campbell).
In the Supernatural episode, “The Usual Suspects”, Blair played police detective Diana Ballard. Although initially interrogating the Winchesters, she later becomes an ally. At the end of the episode, Ballard turns a blind eye and lets the brothers go.
Episode: “Roadkill” (2×16)
Canadian actress/former model Tricia Helfer played Number Six on Battlestar Galactica (2004-2009).
She later portrayed “Charlotte Richards” on Lucifer throughout its 6-season run from 2016-2021.
In the Supernatural episode, “Roadkill”, Helfer played “Molly McNamara”, a central character in that story.
Molly is a ghost, who, unaware of her own death, continued to haunt the road where she died. With Sam and Dean’s help, her spirit is finally at rest and she moves on.
Sterling K. Brown
Episode: “Bloodlust” (2×03) and “Hunted” (2×10), also returns in Season 3
Future Emmy-winning actor Sterling K. Brown played hunter “Gordon Walker” in 4 episodes, beginning with “Hunted.”
Although initially hitting it off with Dean, Gordon later develops a deep hatred for Sam. Gordon believes (accurately) that something is different about Sam and that he may not be fully human.
While Gordon made four appearances, Brown’s contract on Army Wives prevented even further episodes.
In 2016, Brown won an Emmy for playing “Christopher Darden” on The People vs O.J. Simpson: American Crime Story. The following year, he won his second Emmy for playing “Randall Pearson” on NBC’s This Is Us. Brown also won a Golden Globe for his performance as Randall.
Meanwhile, Brown also notably appeared in Marvel Cinematic Universe (MCU) film Black Panther, playing “N’Jobu”, Killmonger’s (Michael B. Jordan) father.
Episode: “Nightshifter” (2×12), later returns for a Season 4 episode
If you’ve watched just about any genre show filmed in Vancouver, you’ll know Chris Gauthier’s credits. His many appearances include Eureka, Once Upon A Time, Smallville and Netflix’s A Series of Unfortunate Events, to name a few.
On Supernatural, Gauthier portrayed “Ronald Reznick”, a conspiracy theorist of sorts. Ronald’s believes that his co-worker Juan, who committed a robbery, had been impersonated by a “mandroid”. Instead, a shapeshifter took Juan’s form.
Of course, Ronald’s investigation eventually intersects with Sam and Dean. From there, craziness ensues from multiple switches, shoot-outs and a hostage situation. As you may expect, not everyone makes it out alive.
Episode: “Hollywood Babylon” (2×18)
Best known for portraying Bob Pinciotti on That ’70s Show, Don Stark makes a brief appearance on Supernatural Season 2.
However, his other roles include playing “Oscar Kinkade” on VH1’s sports drama Hit The Floor from 2013-2018.
Stark played “Jay Wiley”, a film executive producer in the episode “Hollywood Babylon”. Unlike his starring role on That ’70s Show, Stark’s time on Supernatural is short and sweet.
That being said, Stark’s connection runs through the later Supernatural character “Don Stark”. Played by Buffy alum James Marsters (Spike), this witch appears in Season 7 alongside his wife Maggie, played by Buffy’s Charisma Carpenter (Cordelia Chase).
Episode: “Simon Said” (2×5), “All Hell Breaks Loose: Part 1” (2×21)
Tigerman played “Andy Gallagher” (a “Special Child” much like Sam) in two episodes of Supernatural. In his first appearance, he encounters Sam and Dean while using his persuasive abilities to get whatever he desires. However, he becomes friendly with the brothers and they part on good terms.
Andy returns just 16 episodes later, where he, Sam and three other “Special Children” face each other in a battle to the death. Of course, all of this has been orchestrated by Azazel (Frederic Lehne), or the “Yellow-Eyed Demon.”
Tigerman’s other credits include the feature film Charlie Wilson’s War, starring Tom Hanks. His TV guest spots range from Good Luck Charlie, Bones, Hot In Cleveland and Rizzoli & Isles.
Charles Malik Whitfield
Episode: “Nightshifter” (2×12, first appearance), returns in later episodes in Seasons 2 and 3
Special Agent Victor Henrickson presented a unique challenge for the Winchesters. Unlike the countless demonic creatures they faced, Henrickson was an ongoing human antagonist.
He’s played by Charles Malik Whitfield, known for playing “Otis Williams” in The Temptations (1998). His other pre-Supernatural TV roles include a starring role on The Guardian, as well as a guest spot on Homicide: Life On The Street.
Of course, the Agent was just doing his job, believing he was chasing dangerous criminals. The show, however, puts the audience on the Winchesters’ side, meaning they view Henrickson as a ‘bad guy’ in this scenario.
Whitfield reprises the role in other episodes throughout the second and third seasons. Ultimately, as is the case on Supernatural, his arc comes to a sudden, shocking and dramatic ending…
Richard Speight Jr
Episode: “Tall Tales” (2×15) – first appearance, further episodes throughout the series
Perhaps fittingly, The Trickster (aka Gabriel) subverts audience expectations when he first appears. Initially, actor Richard Speight Jr portrays a Janitor, an apparent mortal who witnessed the episode’s murder.
It’s a brief, few lines character type that almost every episode uses. Generally, most people Sam and Dean interrogate either end up dead, a villain or have nothing to do with the case.
However, towards the end, the Janitor is revealed to actually be a Trickster – a creature who can influence what people see and experience. Although presumed dead by the brothers in “Tall Tales”, Speight Jr returns in later episodes.
As well as his recurring role, Richard Speight Jr also directed 11 Supernatural episodes from Seasons 11-15.
Episode: “Hunted” (2×10), “All Hell Breaks Loose: Part 1” (2×21)
Known for playing “Ginger Fitzgerald” in the cult Ginger Snaps film trilogy. Katharine Isabelle portrays Special Child “Ava Wilson” in two episodes of Supernatural Season 2.
In her first appearance, Ava seems to be an otherwise ordinary woman. She uses her psychic abilities to warn Sam of his impending death. However, Ava disappears at the end of the episode, her whereabouts unknown until the Season 2 finale.
So, what happened? Ava wound up in Cold Oak, South Dakota, where she meets (and later kills) other Special Children who arrive there. Sam, Andy (Gabriel Tigerman), Jake (Aldis Hodge) and Lily (Jessica Harmon) are the latest batch.
Despite her prior acquaintance with Sam, even he almost becomes one of Ava’s victims until Jake makes the save.