In one attempt to find the Winchester Brothers, Gordon Walker interrogated their on-and-off ally, con artist Abbie Talbot (better known as "Bela"), played by Lauren Cohan. Graduated and moved to Los Angeles in the summer of 2003. Best known for: Now, Minnette, who also played Jerry Grant Jr. on Scandal, is best known for playing Clay Jensen on the hit Netflix series 13 Reasons Why. He offers Becky another deal: 25 years of Sam's undying love for her soul. Starting off as the first known human vessel of Ruby, a demon who becomes a frequent ally to the Winchester Brothers and love interest of Sam, Cassidy's character's body would eventually be taken over by a white-eyed demon named Lilith, who is most definitely not an ally to the Sam and Dean, but used her new appearance to insidiously achieve their trust. Perhaps you remember the time 1980s music icon Rick Springfield played a rock star possessed by Lucifer himself, or The Exorcist star Linda Blair’s spot as as a skeptical police detective, or even when Paris Hilton dabbled in self-mockery as a demon-possessed version of herself. Supernatural role: Palicki first appeared in the pilot as Jess, Sam's college girlfriend. Becky eventually pretends to accept Guy's proposal. Sort: Relevant Newest. Attended Carnegie Mellon University in Pittsburgh, Pennsylvania. Suddenly Jackson shows up and knocks the three hunters back, and then breaks the pentagram. Best known for: Although Drew started her role on Grey's Anatomy in 2009, it'd take a few seasons before April Kepner caught on. Unfortunately, his role was tragically cut short when he passed away at 31 due to a combined overdose of alcohol and heroin. Despite occasionally turning good to help Sam and Dean, her redemption moment came to a bitter end after betraying the brothers, costing her whatever protection they could have provided once her devilish bargain expired and allowing her soul to be taken by Hellhounds. Born in New York. Supernatural role: In 2007, Spiridakos played a nurse in the season 3 episode "Bedtime Stories.". Yet, before either of those projects came her way, the model/actress also played quite a "hellraiser" (more literally speaking) in the Season 4 Halloween episode of Supernatural, in which she starred as Tracy Davis, a 600-year-old witch performing human sacrifice to resurrect the evil demon Samhaim (actually pronounced correctly in the episode). Over the years, she'd star in four episodes total. In the two-part Season 2 finale of Supernatural, he played Jake Talley, a US military officer who possesses the ability to manipulate others with mind control as a "Special Child," but that did not stop him from falling prey to the wishes of the Yellow-Eyed Demon, Azazel, and become one hell of an obstacle for Sam and Dean. Look for his name in just about any article related to Batman. Best known for: One year after the Supernatural pilot, in 2006, Palicki started her run as Tyra on Friday Night Lights. Posing as a reunion planner, Guy begins making deals in town. Crowley explains that if word got out about that Guy was cheating his clients, no one would want to make deals with the demons and leave Hell with nothing. Guy's fate is not revealed, but given that Crowley stated he intended to make an example of him, Guy was probably killed or imprisoned for all eternity. More than a decade earlier, the then 15-year-old actor made his screen debut on the second ever episode of Supernatural, called “Wendigo,” as Ben Collins, a young man looking for his missing older brother in a Colorado forest with his older sister, Haley (Gina Holden). Guy is a Crossroad Demon who cut his deals short. Believe it or not, however, the Canadian actor had a career before the Hulu exclusive series, which includes a brief guest spot on the second season of Supernatural in which he plays Matt Harrison, the unfaithful boyfriend of Angela Mason (Amara Zaragoza), and her first victim after she resurrects from the dead as a vengeful zombie. Best known for: Thirteen years after his Supernatural role, Ehrenreich played a young Han Solo in Solo: A Star Wars Story. Supernatural role: In 2008, Milligan had a memorable part as Corbett in the beloved "Ghostfacers" episode. Supernatural role: Ehrenreich guest-starred on the second episode of Supernatural, "Wendigo," as the brother of a missing person. Best known for: Now Cassidy is best known for her work on another CW show: Arrow. What helps Gary Cole stand out among the rest of the of the actors on this list is that, by the time he landed his guest spot on Supernatural, he had pretty much already established himself as a prominent onscreen presence, especially as Bill Lumbergh, cinema's quintessential boss from hell, in the classic 1999 comedy Office Space. Supernatural role: Cassidy had a recurring arc as the original Ruby during Supernatural’s third season. Aside from just being regular demon evil, Guy is extra bad because he likes to renege on his deals early. For more information and updates on Supernatural, as well as more A-listers who made early appearances on your favorite shows, here on CinemaBlend. Playing a younger version of Harrison Ford’s iconic space pilot in the 2018 prequel Solo: A Star Wars Story made Alden Ehrenreich a household name. Leslie Odom Jr. Robin Kahnmeyer: Guy: 1 Episode: Nicole Fraissinet Claudia Schmidt: Jocelyn Caruso: 1 Episode: Jason McKinnon Rainer Fritzsche: Brandon: 1 Episode: Olivia Cheng Luise Helm: Leviathan / Susan: 2 Episoden: Sean Rogerson Martin Kautz