Supernatural's Dean Winchester Vs. White Collar's Neal Caffrey: Bad Boy Quarterfinals Continue!

The matchups just keep getting tougher as we reach Day 2 of the TV’s Ultimate Bad Boy Bracket Tournament Quarterfinals.

Yes indeed, brace yourselves for a brutal battle between Supernatural‘s Dean Winchester and White Collar‘s Neal Caffrey!

Every day for the next week, we’ll kick off a new set of matchups in a single-elimination format that will whittle our field down to one ultimate champ. So make sure the right choice is made by heading down to our polls to vote for your favorites (Quarterfinal voting will be open for 48 hours), and hit the comments to justify your picks.

If you’re wondering what criteria we used to pick our players, we cast our net rather wide — including fellas who are dark and a little bit dangerous, truly good guys with naughty, maybe even promiscuous streaks, and actual evildoers who are nevertheless tough to root against.

And if you’re interested in the match-ups that have already finished, and those we’ve got planned for the coming weeks, CLICK HERE TO CHECK OUT THE ENTIRE 64-PLAYER BRACKET (then click again for a zoomed-in view) — and sign up to follow me on Twitter @MichaelSlezakTV. Now ready, set, vote!


Comments are monitored, so don’t go off topic, don’t frakkin’ curse and don’t bore us with how much your coworker’s sister-in-law makes per hour. Talk smart about TV!

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271 Comments
  1. Ruby says:

    Whoa, Neal is winning over Dean? What is this world coming to?

  2. DublinKelso says:

    impossible decision!they both rock and are just beautiful!!

  3. GDV says:

    With Eric Northman and Logan Echolls out of the running, my heart’s just not in it anymore. Spike better win it all.

  4. Kvivik says:

    Go NEAL!!!!!

  5. GD says:

    I thought for sure these would be the two in the finals together. Which ever one wins this race should win it all.

  6. Neal FTW says:

    My husband (!) said it all the first time we watched White Collar: “Prettiest. Man. Ever.”

  7. Miriam says:

    This is impossible.

  8. Mikaylah says:

    I LOVE Matt Bomer as Neal Caffrey, but Jensen Ackles as Dean Winchester is my favorite.

    • Mikaylah says:

      I just looked at the full bracket… If Damon Salvatore wins the tournament, I am done voting in these things. Lol.

      • Hmmmm says:

        I just vote for fun now and then, but I have to agree that a Damon win will seem a bit too forced by the way the brackets were set up. Besides, does a character count as a bad boy if he was only a bad boy for part of a season two years ago? Just curious.

  9. Kara says:

    This was really a hard choice but I have been a fan of Jensen for years. Had to go with Dean.

  10. TigerNightmare says:

    I like Matt Bomer a lot more as Bryce Larkin.

  11. Robyn Pennington says:

    It was hard but I ended up going with Dean. He’s been to hell and back and even survived the apocalypse. Neal lost in my book because he’s a) high class and b) he’s reformed. Dean is just a long suffering man who, to my surprise, still has a soul – barely.

    • Shannon says:

      You said it! I love both of these boys but my loyalty is with Dean hands down! I will be shocked if fandom doesn’t rally and send Dean over the top.

  12. Jared says:

    Omg! How do u choose between these two!!!!! I don’t want to! Don’t make do it!!!! Lol

  13. Ace says:

    You really want me to choose between these two lovely, talented, TEXAN boys? Nope, can’t do it. I’ll have to vote for one from my work PC and one from my Mac at home!

  14. John says:

    This is an impossible woman-heavy poll.

  15. V says:

    Noooooo!!!!! Neal vs Dean?!?!

  16. Susie says:

    Neal Caffery. Complex and nice to look at!

  17. Laura says:

    A date with Dean – sitting in a dive bar watching him brood and drink, followed by really good sex. A date with Neal – wined and dined in style, followed by really good sex. I’ll take Neil.

    • Ema says:

      It’s easy to be wined and dined, any sleaze looking to get a girl into bed can do that(not saying Neal is a sleaze, he clearly isn’t, just sayin’ winin’ and dinin’ is easy), with Dean, if you manage to live through the date without being kidnapped or killed by a monster, it’s going to be something unique that you’ll never forget. LOL Plus really good sex. :D

    • Hyde says:

      you just answered your own question… a good date does not equal “bad boy” it equals nice guy. a bad boy will pick you up in a dive bar, take you home in a bad ass car or motorcycle, f*** your brains out three ways from sunday then never call you again.

      • alyssa says:

        A bad boy doesn’t even have to take you home. He’ll just do you in the back seat of his bad ass car with some led zeppelin playing in the background and then be done with it. And I think the only man I would ever be fine with doing this to me…is Dean Winchester. Which is why I voted for him. :D

  18. Bella says:

    Brutal is right. I’m sure setting these match-ups was tough, but it seems like some of them get cake-walks, while others like this one, are almost impossible to pick between. Two completely different men and each terrific in his own way.

  19. Brittney says:

    NO I can’t choose. They should both be in the finals.

  20. Dean Girl says:

    Matt is hot and good as Neil, BUT he isn’t Dean, played by the extremely handsome Jensen.

  21. Mike says:

    I can’t believe I have to make this choice. These two would be my final two!

  22. Andie says:

    COME ON DEAN!!!!!!!!!!!!!!!!!!!

  23. Ashley says:

    Neal. Neal, Neal, Neal, Neal, Neal. Did I mention Neal? Love him! He definitely deserves to take this round!

  24. Ryan says:

    Both are awesome, but they’re different kinds of “bad boys.” Neal is literally a conman, whereas Dean is badass. Hard choice, but Neal wins for me. The charm and class complement his cunning side.

  25. As a HUGE Supernatural fan, I have to say that Dean is not a bad boy. He’s the ultimate good boy with an edge. He’s totally selfless and saved the world and put himself to hell and back for the greater good. No bad there, just a little cheeky with woman ;)

    • Kate says:

      While I agree that he almost always has good intentions, you can’t deny that he’s made morally/ethically questionable choices. Torturing/killing demons while in their innocent human hosts, selling his soul, becoming a torturer in hell, killing Amy this past season, etc. To me that makes him more of a bad boy than Neal really. I mean yeah Neal steals things. But he steals things from very rich people who can afford to lose them and he’s never killed or tortured anybody.

      • Emily says:

        So your definition of a bad boy is… Jack Bauer?

        • Kate says:

          I didn’t watch 24, so I don’t know much about that character. But yes, I do consider someone who has actually killed/tortured people/sentient beings as more of a “bad boy” than a pretty conman/thief. How is that odd?

  26. April says:

    This is harder than Dean vs. Mal!

  27. Jessica says:

    Neal is my bad boy! ;)

  28. bfeld says:

    NEAL ALL THE WAY!!! Beyond awesome character and actor! And plus Matt is just the nicest Guy! I met him 3 times!

  29. CJ says:

    No one is better at being bad and making it look good than Neal Caffrey!

  30. Kate says:

    I love them both, but I went with Dean because he’s way more of a bad boy (and a badass) imo. I mean as far as we know, Neal has never actually killed anybody/anything.

  31. Jill says:

    Tough choice here! Love them both, but Dean kicks ass while Neal is smooth.. Dean for me!!

  32. Lili Carmona says:

    DEAN, DEAN, DEAN, should WIN, WIN, WIN!!!!!

  33. Matt Anthony says:

    Close call but Dean is the winner. Hope Dean pulls through the poll. Bye the way Tom Welling is better looking than Matt Bomer. Just wish he was acting right now.

  34. deborah says:

    Dean vs Neal, huh? DEAN! DEAN! DEAN!!!!

  35. W says:

    What’s the deal moderator?????? I voted like 10 times and I got blocked for a cooling off period.

    • AJ says:

      I believe you can only vote 1 time, and that’s good. That’ll keep people like you from voting dozens of times for your favorite character.

      • Temis says:

        Hmm I’m not so sure. I just voted about 12 times in a row to kick Dean ahead of Neal. Unless everyone else righ now is voting for Dean too, I think that was me. I’m on an iPad, does that make a diff?

        • W says:

          I was voting for Dean trying to get him ahead of Neal. The poll won’t even let me view the results citing suspicious activity. WTF?

        • Emily says:

          I’m super confused. How does being a more rabid voting fanbase prove anything? It just invalidates the results.

          • tripoli says:

            Exactly. But the rabids are also voting based on who they think is the dreamiest, so any result is suspect at best.

          • It shows how wonderful the person or show they are voting for must be… for it’s fans to be SO ‘rabid’ about them that they will put in all this effort.

          • Emily says:

            Then SPN fans complaining that cheating must be involved for Matt Bomer to pull ahead is the definition of hypocrisy. WC fans are just “putting in the effort,” after all…

      • Hmmmm says:

        I just tried to vote again to see if it can be done and I am not allowed to as “my vote has already been counted.” perhaps, people are just trying to start fan wars?

    • Ema says:

      No one has been voting ten times in a row, it sounds like someone just didn’t notice the message that comes up after you’ve voted once saying that you’re vote has already been counted and then after ten times suddenly did. Or someone is lying trying to start a fan war. But at no point have I or anyone I know been able to vote more than once by simply voting again.

  36. Tricia says:

    Why don’t we just let them fight it out?

    • Ema says:

      They are both Texas boys of around the same age and Ackles only has an inch or two on Bomer in height, it would probably be a pretty fair fight. Whose up for a Jensen Ackles/Matt Bomer Cage Match?!!!?!! LOL

      • Hyde says:

        Only if we can have it in jell-o!

      • Patsy says:

        Actually Matt is almost 6 ft just like Jensen. Jensen has maybe 1/4 inch over Matt because Matt is 5 ft 11.25 inches. And that .25 is just more hotness to love. Both men are hot but I think Matt is a bit higher on the rictar scale for sophistication, class & overall aesthetic beauty. He is the next George Clooney, watch him soar. Good match up though, they both should win!

  37. W says:

    Come on voters, there is no comparison between Dean and Neal. Vote Dean Winchester. BTW – What about Daddy John Winchester? I love me some Daddy Winchester.

  38. shiran says:

    Dean is more of a bad boy then Neal. Sorry..

  39. Michele says:

    I love both – but I think Neal is a TINY bit more of a bad boy.

  40. mickey22 says:

    While I do Like Matt, I LOVE Jensen!

  41. Roxy Pitt says:

    It was a hard decision but in the end I had to go with my Deany!!!!

  42. Roxy Pitt says:

    I was a hard decision but in the end I had to go with my Deany!!!!

  43. this vote was heartbreaking i am sorry matt no matter how much i love you jensen was my first!!*deangirl since 2005*

  44. cherin says:

    of course dean winchester cause he’s my bad boy

  45. samrenee2010 says:

    Neal hands down!!!!

  46. Samantha says:

    My favorite eye candy vs my television crush. Michael, you are too cruel. Matt’s better looking, but I gotta give Jensen the edge.

  47. Kira says:

    Dean could murder Neal 18 times before he finished putting on his fedora. Get ‘em, Winchester! (Jensen Ackles can also act circles around Matt Bomer.)

    • Petei says:

      LOL – that’s why Matt has just finished two movies with top Directors and will begin filming two more in September while J will be stuck on the CW!

      • Hyde says:

        that doesn’t mean he can act, I mean, did you see Bomer on Glee? That was a trainwreck. It was like he was parodying the whole time instead of being a character. There are some actors that are amazing on tv and some that are amazing on big screen. Bomer is mediocre at best at both. Jensen excels at tv but has made some questionable movie choices, but if you notice, it wasn’t his acting that killed the movies, but the writing or plot themselves that were barfy. I can’t get behind Bomer, he’s just a face to me. He should just model. (of course, this is all MY opinion)

  48. Who’re you all kidding? Dean’ll win this. he’s the biggest, baddest mofo ever!

  49. Melody Paris says:

    This one kills me, these are my two favorite guys on TV….but I have to give it to Dean I just think he’s more of a bad boy.

  50. saxyroro (@saxyroro) says:

    Dean. NEXT!

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