Supernatural Chat: Top 10 Funniest Characters

Supernatural may show up in TV listings as a “Paranormal Drama” (at least it does on my cable network listings), but one of the things I dig about it is the fact that in between the angst and the drama, and underneath the scares, there’s a whole lotta humor.

So this week I decided to take a look at my top 10 funniest characters on Supernatural. Keep in mind that I’m not judging these characters on love or even their worth on the show; otherwise this would probably be a very different list. No, this is based purely on their comedic value and how many times each of them has made me laugh or has the ability to make me laugh with just a line, a look, or even just by walking into a room.

Andy Gallagher

Supernatural - Andy

Played by Gabriel Tigerman, Andy was a guy who may not have appeared in a lot of episodes but when he did, he totally cracked me up. One of my favorite lines from season one is his: “I can’t calm down! I just woke up in freaking Frontierland!”


Okay so yeah, Lucifer may not be the first character someone thinks of when they think of comedy on the show and I’ll admit that his first appearances were more dramatic and maybe a touch melancholy. But once Lucifer made himself comfortable inside Sam’s head he suddenly grew one heck of a sense of humor. The scene where he’s reading symptoms of narcissistic personality disorder and debating on which ones he had…that was some pure comedy right there.


Really? Do I need to say more than just Ash’s name? From the haircut, to the beer-chugging, to the gratuitous nudity – Ash was a really funny guy and I still miss him. Though the fact that we saw him once in Heaven and he was still acting like his old hilarious self has me hopeful that maybe, just maybe, we’ll see him again someday.


Yet another character that I miss is Chuck. Sure he had one of the best exits of any character on Supernatural (disappearing in a puff of smoke leaving us convinced he was God). But before all that mystery there were a ton of laughs. Pretty much everything he said in “The Monster at the End of This Book” was hysterical and who can forget him finding Cas’ tooth in his hair? Like I said, hilarious.


Finally a character on my list who’s not dead or has mysteriously disappeared for who knows how long. We only met Garth this season but he’s already one of my favorites. He’s one of those characters who can crack me up with just a look, let alone when he starts talking. The fact that Garth thinks he’s the coolest cat on the planet just adds to his charm, and to the hilarity he brings on screen.


Ed and Harry made their first appearance on Supernatural back in season one, in an episode that was already pretty funny (Sam and Dean in a prank war). But they managed to add even more humor and when they got their own special episode, I loved it. That episode allowed us to see Sam and Dean do things they never do normally, like curse and give obscene finger gestures. It’s also one of the scariest episodes I’ve ever seen, but thanks to the Ghostfacers crew, it’s also one of the funniest.


Supernatural Plucky Pennywhistle's Magic Menagerie Season 7 Episode 14

When I first started watching Supernatural, I don’t think I would have ever labeled Sam as a funny character. Sure he had his moments here and there, but it was Dean who was given all the real broad one-liners. But while Sam’s humor is different, after a while I realized that it was also pretty darn funny. Jared’s entire performance in “Bad Day at Black Rock” is one of the funniest things I’ve ever seen and who can forget his wonderful delivery of: “I lost my shoe.” Sam’s humor may be more subtle than Dean’s, but when the moment is right, one of his little side comments can sometimes make me guffaw harder than one of Dean’s straight up zingers.


Supernatural - Bobby in Weekend at Bobby's

Bobby Singer is a gruff guy (yes, I still refer to him in the present tense), but it’s that gruffness that makes him funny to me. Bobby is the guy who can put Sam and Dean in their place with just a few choice phrases and I get such a kick out of the way he calls them “idjits.” Even when he was a ghost, Bobby still cracked me up. It’s often his frustration with his boys that makes him spout off some really great lines.


Supernatural Season Finale 2012 Survival of the Fittest

When Castiel was introduced, he wasn’t exactly Mr. Funny, but with his innocent angel-eyed view of the world, his scenes quickly became some of the most hilarious on the series. Between his puppy dog head tilts when he didn’t understand something, to calmly sitting on a whoopee cushion or frantically chugging a beer in a brothel, Cas can usually make me laugh harder than almost anyone else on this show. That being said, I hope we lose the really silly version of Cas soon. I found his more subtle humor much funnier than the goofball we were left with at the end of last season.


Jensen Ackles as Dean

Dean Winchester was the very first character that made me laugh on Supernatural and if you read my last article, then you know that he was integral to my falling in love with the show in the first place. Dean has great one-liners and his snarkiness is on a level all its own, but I also get a kick out of the fact that this big, strong tough guy can also deliver some hilarious pratfalls and other physical comedy. From dressing up in wacky costumes (gym coach, lederhosen) to falling victim to some crazy supernatural diseases, Dean has easily delivered more laughs for me than any other character on this show.


What about you folks? What characters have made you laugh the hardest on the show? Sound off in the comments below. I love hearing from you guys!

”Supernatural Chat” is published every Tuesday. If you’re curious what this column is all about, check out our introductory post on it and more articles here.

Follow me on Twitter @mokibobolink

  • Umm… where’s Crowley?

  • Mandy

    I agree dean is definitely had me laugh then another character. Good list!

  • KB

    Good list–especially saving Dean as the best for last. 

    I would add that hilarious waiter, Brandon, from How to Win Friends and Influence Monsters.  He was in only the one episode, but three of his scenes kill me every time I see them.  Telling Dean off, the whole Big Bird, Ken Doll, and Creepy Uncle scene and then that hilarious hand gesture he does when he tells his boss off. 

  • jenny

    How can this list exist without Crowley, Balthazar, or The Trickster/Gabriel?!

  • I really doubt, if the person who ever has created the list, watched the show at all. Because he/she missed Crowley, who deserves number one position and also included Castiel in the list who was never funny as far as I am concerned. Where is Gabriel? Where is Balthazar? I guess they are certainly funny than many characters mentioned here in the list. Andy appeared hardly for in 40 minutes in this 149 episode series. Does he really matter?

  • Deborahlb58

    So agree with you concerning Castiel and Dean!!  I  LOVE them!  Both Castiel and Dean can offer not only stellar dramatic moments, but also moments that leave me laughing my head off.  I also hope that we get the ‘original’ more subtle humor of Castiel back in season eight, as I did not care too much for the crazy act of season seven, either. 

    With regard to the rest of the list, I would replace Andy and Garth with the Trickster/Gabriel and Crowley. Neither Andy nor Garth can hold a candle to the sometimes comedic Crowley and the often hilarious Trickster/Gabriel (“Changing Channels”).

  • How can Gabriel not be on this list?  0_o

    • nadine

      I agree!!!!!!!! He such have at the top of the list.

  • Mickey

    It’s funny how on the show Sam is the straight man and Dean is the goofball, but in real life, Jensen is the straight man and Jared is the goof ball. Sometimes a funny line from the straight man is even funnier, because it comes from the straight man, an unexpected and contrasting source.

  • Denise

    I love your list, although I do have to agree with pretty much everyone here about Crowley. Even his first scene with Sam and Dean when Sam points the colt at him and shoots, then Crowley, without blinking an eye says ‘Oh yeah, you’re going to need amunition.” Since then he’s delivered great one-liners and is always there with a witty retort.
    Also, I totally back you with Andy. He really was funny. My favorite scene with him was at the research library, holding his head and quietly saying…”I have an….evil…..twin.” Sadly, as with most SPN guest stars,he was killed off too quickly, but what little time he had with us was completely entertaining.
    Also love Bella. Her spitfire attitude and quick witt made her a great adversary for Dean. Loved the “I sleep on satin sheets, naked and rolling in money.” line the best. She held her own as far as comedy was concerned.
    Thanks for the article. As usual you won’t please everyone, but that’s par for the course!

  • Dreamyeyes1

    Frank, Gabriel, Balthazar, Crowley, Rufus!!!!!!

  • Dreamyeyes1

    And fangirl Becky and the LARPERS Damien and Barnes!

  • Pepsiipj0106

    Dean was the funniest at first lol..then sam came along with “i lost my shoe” and then dean came along with “im batman” then castiel with “hey assbutt” (also after that he got more funnier lol ….Dean,Sam,&Castiel were the funniest to me 😀

    • Pepsiipj0106

      I meant (also after that castiel got more funny lol)