Supernatural is currently in its thirteenth season with a possible spin-off show and fourteenth season looming on the horizon. It has the loyalty and adoration of a fan base that doesn’t plan on changing the channel on Sam and Dean Winchester anytime soon. The popularity of the show has spawned its own Supernatural themed conventions along with a whole section of Hot Topic devoted to t-shirts and other merchandise featuring the hunters. Jared Padalecki and Jensen Ackles have played the brothers for over a decade, but they weren’t always fighting off apocalypse after apocalypse.
Before Supernatural gave the boys their big break, they had to endure a journey that every actor must face. They went down a path of embarrassing and cringe-worthy roles that each of their co-stars also followed. Some of these roles occurred in direct-to-video films and television movies or shows. Some starred on ‘90s powerhouse sitcoms like Boy Meets World and Doogie Howser in roles you wouldn’t expect them to play. There is even one performer who starred in their own educational video on taxes. Either way, you’ll be giddy to watch some of the roles that your favorite gang of ghostfacers played before their Supernatural stardom.
15 KURT FULLER IN SCARY MOVIE
Kurt Fuller played the angel Zachariah on Supernatural. He was a sinister character that wanted to release Lucifer and unleash the apocalypse on the world so that paradise would be restored on Earth. Fuller played the self-interested angel intent on killing everyone on the planet with a cool that was dead-eyed and unsettling at times, but he wasn’t always so menacing.
Before Fuller donned his wings and terrorized the monster-hunting brothers, he played the pervy Sheriff in 2000's comedy hit Scary Movie, a film that parodied horror and slasher films of the ‘90s. Fuller's Sheriff character constantly asked teenagers inappropriate questions while also subjecting them to look at and critique photos of himself wearing a speedo. It was meant to be comedic, but it just comes off as uncomfortable and odd to watch.
14 CHAD LINDBERG IN BORN TO BE WILD
Some might consider Chad Lindberg’s role as the mullet-loving drunk genius Ash as an embarrassing one, but to Supernatural fans he was one of the most beloved characters on the show. Lindberg’s slapstick qualities and matter-of-fact delivery always landed jokes well while grounding him whenever Ash needed to get serious. It was a range that made fans think twice about underestimating Ash before he died in a fire that burned down the Road House.
Lindberg’s roles weren’t always this rich, as evidenced by his appearance in 1995’s Born to be Wild.
In the family comedy featuring a boy trying to rescue a gorilla, Lindberg played a character credited as Burger Boss. It’s a small part, but Lindberg gives it his all as a disgruntled fast food employee who couldn’t care less about a gorilla in his drive-thru and just wanted to know if the food was paid for.
13 ALONA TAL IN TAKING 5
Alona Tal wasn’t always the badass hunter and daughter of Ellen who helped Sam and Dean stop the apocalypse. Her character Jo Harvelle fought off H.H. Holmes’ ghost and added a younger perspective to the Supernatural mythos. Before Tal picked up the sawed-off shotgun and salt rounds, she starred in a teen comedy with a character that was the antithesis of Jo.
Tal played Devon Thompson in a movie called Taking 5, where she and her friend are infatuated with a popular boy band played by one-hit wonders The Click Five. High school was going well for them until Tal’s character lit a cheerleader’s hair on fire and lost her and her friend’s chance to meet the band. They become social pariahs, but come up with a plan to get in the school’s good graces by kidnapping the pop band and forcing them to perform at school. It's absolutely ridiculous.
12 SAMANTHA FERRIS IN BEGGARS AND CHOOSERS
Jo’s mom Ellen was another fan favorite, who Samantha Ferris embodied just as well, if not better, than Jim Beaver as Bobby Singer. She was a matriarchal figure to the boys when they needed one. Each scene that featured Ferris held a weight of dramatic tension that only a performer like her could truly bring to the screen. Supernatural is filled with life and death, but Ellen’s concern and love for those around her helped alleviate that tension.
Most fans would never remember a show titled Beggars and Choosers that followed the behind-the-scenes lives of Hollywood, but this Supernatural alum had a recurring role in it. It was a silly and raunchy show that unfortunately had Ferris playing a sleazy actress who is super self-absorbed. Her character literally has dozens of photos in her office with her own face on them.
11 LINDSEY MCKEON IN SAVED BY THE BELL: THE NEW CLASS
Lindsey McKeon’s role on Supernatural was of an elusive grim reaper named Tessa, who was in charge of crossing souls over to the afterlife. She first appeared in the second season opener, but she wasn’t always a minion of Death! She actually starred in the Saved by the Bell revival show, The New Class, where she played Katie Peterson, the Jessie Spano archetype of the new era.
Her portrayal never reached the same heights of her successor, but neither did the show as a whole.
Katie Peterson's character always seemed to be put in the background as much as possible. Mostly, McKeon always looked like she’d rather be anywhere else, but on set. It’s almost uncomfortable watching the whole cast try to bring back the spirit of the original series.
10 TRAVIS WESTER IN EUROTRIP
Ghostfacers! Travis Wester wasn’t always an amateur paranormal investigator and documentarian named Harry Spangler. In fact, he was a different kind of a nerd in his appearance as Jamie, a lover of European history, in the 2004 raunchy classic EuroTrip. The character is reminiscent of Spangler as the two characters are awkward and sheepish.
This Ghostfacer traveled through Europe trying to help his friend Scotty find his German pen pal Mika, who he realized he’s in love with after finding out she was a woman. It’s a journey that turned into pandemonium as most of these early 2000s teen comedies did. It had Wester be touched inappropriately by a younger Fred Armisen, featured him kissing his character’s twin sister, and screaming incessantly from one side of Europe to the other!
9 NICKI AYCOX IN BOY MEETS WORLD
Nicki Aycox’s Meg terrorized Sam and Dean throughout the first and second season of Supernatural as the daughter of Azazel, the yellow-eyed demon himself! Before Aycox had her run-in with the demon that possessed her, she was featured on a ton of television shows as a guest star.
One of those shows she appeared on was the beloved ‘90s hit Boy Meets World.
She played a college student that fell in love with Shawn Hunter and his philosophical mind. The only problem was that Shawn Hunter was still in high school. Her ditzy demeanor and fawning over the teenage heartthrob is just so over the top that it doesn't match up to her portrayal as the demon who gave the boys a run for their money in Supernatural.
8 ADRIANNE PALICKI IN POPSTAR
Adrianne Palicki’s Jessica Moore was the second woman in Sam Winchester’s life to have her body pinned to the roof and set on fire by the yellow-eyed demon Azazel. His mother shared the same fate. It wasn’t until the year after that she became a huge television star on Friday Night Lights as Tyra Collette. Before she ever came close to the flames of Sam’s lost love Jessica, Palicki played a small role in a direct-to-video 2004 movie titled Popstar.
The film pitted her against a nerdy girl for the love of a pop star.
That role was played by early 2000s teen sensation Aaron Carter, who had to go public school with all the other schlubs. She’s mean and vicious in that Mean Girls style of the era without the same tact of that film. She basically plays a less nuanced version of her character on Friday Night Lights.
7 JEFFREY DEAN MORGAN IN STAR TREK: ENTERPRISE
Jeffrey Dean Morgan is now the iconic Negan from The Walking Dead, but before that he played the Winchester's father John Winchester. He was a man fixated on finding and killing the demon that took the life of the mother of his children. Morgan did a great job emoting the pain within John’s vengeful gaze and showing great vulnerability toward his sons, Sam and Dean.
Unfortunately, Morgan didn’t always have the chance to tackle emotionally complex fathers or sadistic psychopaths. Before those roles, he played a Xindi-Reptillian in Star Trek: Enterprise with a whole lot of prosthetics and makeup caked up all over his face. He has confessed that he took the job for money in an interview with the Huffington Post. It was a small time role that helped him pay for dog food and his rent at the time.
6 MARK PELLEGRINO IN DOOGIE HOWSER
Lucifer, played by Mark Pellegrino, is oddly a fan favorite of the show. He has tortured Sam’s soul and even made Castiel go nuts when he possessed him. Pellegrino brings a strange charm to the fallen angel who set up a shop of literal horrors in Hell while waiting until it was his time to bring the apocalypse to Earth.
Before he tortured souls, Pellegrino was bullying kids at the pool hall in Doogie Howser.
The scene has him clad in an early ‘90s style wardrobe which featured a bright multicolored polo and a serious mullet to boot. He dons a dopey expression while fat shaming some poor girl on a date with Howser’s friend. It ends with Pellegrino getting a pool stick to his groin before he falls out of the shot from pain. The extremely ‘90s scene must be witnessed by any fan of the Devil himself.
5 MISHA COLLINS IN NO BRAINER ON TAXES
Castiel’s suit and trench coat have become a staple of the character since he first appeared in Season 4, flexing his wings in front of Dean Winchester. Misha Collins’ first season on the show had him portray a hyper-serious angel who had to stop the apocalypse from occurring. Collins knew how to shift between his biblical wrath while maintaining the curiosity and wonder of an angel walking on earth.
His suit on the show wasn’t the first one he’s needed for a character. He actually starred in the most interesting educational video on taxes we’ve ever seen. Kidding! It’s super boring, but Collins gives it his best. He tries to interest viewers on the wild world of tariffs while throwing out punchlines that would only work on dads at a cookout. It’s a priceless video that you can find on YouTube.
4 KATIE CASSIDY IN LISTEN UP!
People might not remember, but before Katie Cassidy starred in Arrow as Laurel/Black Canary, she was a demon named Ruby on Supernatural. Cassidy's character was a wonderful addition as she constantly saved the boys from monsters that almost killed them. Cassidy's portrayal had a bite that she'd unleash whenever the boys got themselves into a mess. She also knew how to mix her angst with a genuine care for the brothers just when she needed it.
She, like everyone on this list, had to go through her pile of ridiculous roles.
She guest starred as Rebecca on the show Listen Up!, a family sitcom that only lasted one season. Cassidy had a quirky little role that had her donning Civil War reenactment clothing and being completely in love with the era. This wasn’t exactly the action-packed roles that she played in Arrow or Supernatural.
3 GENEVIEVE PADALECKI IN WILDFIRE
Genevieve Padalecki also played Ruby in her second incarnation on the show. She had Sam Winchester drinking demon’s blood to grow the psychic power imparted to him by the yellow-eyed demon. Genevieve gave Ruby a vulnerability that was different from Katie Cassidy’s portrayal. The chemistry between Genevieve and Jared Padalecki grew on and off the screen, which eventually led to the co-stars getting married.
Before they tied the knot, Genevieve had a small stint on an ABC Family show titled Wildfire. Its premise at first sounds like it may center around the juvenile detention system, but quickly starts involving horses?! That’s right! Genevieve’s role as Kristine was one of ABC Family’s odder creations as it had the young jockey go to a juvenile detention center after committing grand theft auto. It also just tried too hard to create a romance that never felt organic. It’s all very early ABC Family.
2 JARED PADALECKI IN A RING OF ENDLESS LIGHT
Sam Winchester just wanted to go to law school and live a normal life outside of the monster-hunting business that his family got him involved in. Jared Padalecki’s portrayal of this Winchester is filled with an angst and anger that any person could identify with. This approach to the role gave Sam Winchester a vulnerability that his brother didn't share.
Before Supernatural, Disney Channel roped Padalecki into playing a bully with a serious amount of privilege.
In A Ring of Endless Light, he had a convertible Porsche and a swagger that barely ever felt authentic. Whenever he showed up on screen, Padalecki tried to flash a smile while prattling off lines like, “I was busy getting thrown out of various prestigious and private schools.” It never seemed to mesh with Padalecki’s overall demeanor, and is sure to make Supernatural fans cringe.
1 JENSEN ACKLES IN WISHBONE
Jensen Ackles teaming up with Scooby Doo for an animated episode on Supernatural sounds exactly like the kind of satirical comedy the show is known for. The craziest part is that this isn’t the first time that Ackles has teamed up with a dog on the small screen. He played a small part on Wishbone back in the '90s with a hairstyle and denim shirt that fit the era.
Michael Duss, the character Ackles plays, is a young man whose mother passed away, but his demeanor is much different than the older Winchester brother. This is the first role of Ackles’ young career and he seems super nervous to deliver the few lines he has in the episode. It is more how fans envision Dean's acting failing in a scene than any Ackles performance in Supernatural.