Before we get to the final 25 familiar faces, I am aware that there are many faces that didn't make the list who were probably expected. Some of those were specific choices, such as Bobby, Castiel and of course, present-time Sam and Dean. For me, these individuals don't qualify as Guests, but rather as the Supernatural core.
 
Hence, they were not on this list. Others of course, simply didn't fit. This was a difficult list to compile, because as I began going through the seasons, there were just so many characters to choose from. So, I tried to select some that we haven’t seen too much recently, but also the ones that needed to make the list. I'm sure I left off someone somebody was hoping would be included - which is why my next endeavour, once season five concludes and we are immersed in, dare I say it, Hellatus (!), will be to complete the list of guests. Now, without further ado, here it is - the final instalment. 
*******************
 
Andy Gallagher


 
Played by: Gabriel Tigerman
First appearance: Simon Said
Most recent appearance: All Hell Breaks Loose, Part I
Last seen: being murdered by a demon after transmitting to Dean their location in Cold Oak
 
 
Rebecca Warren


 
Played by: Amy Grabow
First and only appearance to date: Skin
Last seen: learning the truth about Sam's real life
 
Chuck Shurley a.k.a. Carver Edlund

 
Played by: Rob Benedict
First Appearance: The Monster at the End of the Book
Most recent appearance: The Real Ghostbusters
Last seen: Hooking up with his number one fan
 
Ed Zeddmore


 
Played by: A.J. Buckley
First appearance: Hell House
Most recent appearance: It's a Terrible Life
Last seen: advising on the burning of bodies that is illegal in some, possible all, states
 

Harry Spengler


 
Played by: Travis Wester
First appearance: Hell House
Most recent appearance: It's a Terrible Life
Last seen: offering advice on "ghost-adjacent" problems
 
 
Ash a.k.a. Dr. Badass


 
Played by: Chad Lindberg
First appearance: Everybody Loves a Clown
Most recent appearance: Dark Side of the Moon
Last seen: putting string theory to practical use
 
 
Jamie


 
Played by: Melinda Sward
First and only appearance to date: Monster Movie
Last seen: sending the once again de-hymenated Dean Winchester on his way
 
 
Alastair

 
Played by: Mark Rolston, Christopher Heyerdahl
First appearance: I Know What You Did Last Summer
Most recent appearance: When the Levee Breaks
Last seen: Appearing in Sam's withdrawal induced hallucinations
 
 
Zachariah



Played by: Kurt Fuller
First appearance: It's a Terrible Life
Most recent appearance: Point of No Return
Last seen: being played to death by Dean Winchester (finally!)
 
 
Anna Milton



Played by: Julie McNiven
First appearance: I Know What You Did Last Summer
Most recent appearance: The Song Remains the Same
Last seen: being obliterated by Michael
 
 
War


 
Played by: Titus Welliver
First and only appearance to date: Good God, Y'All
Last seen: losing his ring, keeping his life
 
 
Famine


 
Played by: James Otis
First and only appearance to date: My Bloody Valentine
Last seen: learning what happens when you get on Sam's bad side
 
 
Maggie Thompson


 
Played by Conchita Campbell
First and only appearance to date: Playthings
Last seen: Spiritedly (ha!) playing with her sister
 
 
Lucifer
 

 
Played by: Bellamy Young, Mark Pellegrino
First appearance: Sympathy for the Devil
Most recent appearance: Abandon All Hope
Last seen: surviving death to raise Death
 
 
Trickster a.k.a. Gabriel



Played by: Richard Speight Jr.
First appearance: Tall Tales
Most recent appearance: Changing Channels
Last seen: in a burning ring of fire
 
 
Jo Harvelle



Played by: Alona Tal
First appearance: Everybody Loves a Clown
Most recent appearance: Abandon All Hope
Last seen: dying a warrior's death in her mother's arms
 
 
Ellen Harvelle



Played by: Samantha Ferris
First appearance: Everybody Loves a Clown
Most recent appearance: Abandon All Hope
Last seen: facing evil and kicking it the ass
 
Todd

 
Played by: Ryan Grantham
First and only appearance to date: Wishful Thinking
Last seen: beating up Dean Winchester
 
Mary Winchester

Played by: Samantha Smith, Amy Gumenick
First Appearance: Pilot
Most recent appearance: the Dark Side of the Moon
Last seen: in a shudder-inducing, Zach-loving evil manifestation
 
John Winchester
 
Played by: Jeffery Dean Morgan, Matthew Cohen
First Appearance: Pilot
Most Recent Appearance: The Song Remains the Same
Last appearance: mind-Windexed after an angel infestion
 
Young Sam
 

 
Played by: Alex Ferris, Colin Ford
First appearance: Something Wicked
Most recent appearance: Dark Side of the Moon
Last seen: sharing a moment with his big brother
 
 
Young Dean

 
Played by: Ridge Canipe, Brock Kelly
First appearance: Something Wicked
Most recent appearance: After School Special
Last seen: ready to get out Truman High School
 
 
Old Dean Winchester

 
Played by: Chad Everett
First and only appearance to date: The Curious Case of Dean Winchester
Last seen: turning back the clock
 
Crossroads Demon I
 
 
Played by: Jeannette Sousa, Ona Grauer, Sandra McCoy
First appearance: Crossroad Blues
Most recent appearance to date: Bedtime Stories
Last seen: wishing she'd let Dean out of his deal
 
 
Deacon
 

 
Played by: Garwin Sanford
First and only appearance to date: Folsom Prison Blue
Last seen: having his heart bruised, literally