Not Shounen, Good Guy:
Dendrobates
- Assassin working in the Police for (Desk Position), not the Happy-go-lucky Main Charater either but and he inst the one to rush into things without thinking. (however it most likly not what you're looking for).

Not Shounen, Bad Guy:
Hoshi no Samidare [Completly Scanelated]
- The Main Charater is one of the people choosen to Fight for the protection of the Earth, however he and the Their "Leader" has diffrent plans, being "Weak" he can't just rush into things and needs to plan a head.
Zennou no Noa - The World of Lostmemories [Completly Scanelated]
- Terrorist Main Charater and Genius inventor. He has plans and he carries them out.
Black Lagoon [Ongoing, Up To Date]
- An office worker gone Modern Pirate/Smuggler, He's definetly on the Bad Guy side but he got the Good Guy personality so he get other people to do his dirty work (in simple explenation).
Heat [Completed, Being Scanelated]
- A Guy starts his on gang and clashes with the Yakuza, not something that can be done without the brains for it.
Tobaku Mokushiroku Kaiji [Completed, Not Being Scanelated, Anime Exist]
~ Prequal to Tobaku Hakairoku Kaiji
- He is a Good-for-nothing-nobody who ends up in High-Risk-High-Return gambles in order to clear his debts, When he is backed into a corner he has his sparks of genius.
Tobaku Hakairoku Kaiji [Completly Scanelated]
~ Prequal to Tobaku Datenroku Kaiji, Sequal to Tobaku Mokushiroku Kaiji
- Same Charater, Another Big Gamble.
Tobaku Datenroku Kaiji [Completed, Being Scanelated]
~ Prequal to Tobaku Mokushiroku Kaiji: Kazuyahen, Sequal to Tobaku Hakairoku Kaiji
- Same Charater, Another Big Gamble.
Tobaku Mokushiroku Kaiji: Kazuyahen [Ongoing, Not Being Scanelated]
~ Sequal to Tobaku Datenroku Kaiji
- Same Charater, Another Big Gamble.
Usogui [Ongoing, Being Scanelated]
- A Gambler, an Infamous one, who goes into life and death gambles, How to describe him? Demon, Monster, an Abomination.

I included some even if they didnt fit the your request all to well but rather as long the charater wasn't the headon rush in.

I had to Double Post since I couldn't post it all in one go (didnt work).

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If you want to succeed
Then you don't need Good Luck
You need the ability to overcome Bad Luck

Happines and Light needs a source to exist
Hatred fuels itself and Darkness exist where there is no Light


† Lightmare †

Thanks for these recommendations! I have already read Mx0 and Iris Zero and Kurogane (IKEZAWA Haruto) are among my favorites, but the others look very promising.

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Nulla in mundo pax sincera
"Always go too far, because that's where you'll find the truth." - Albert Camus

Definitely The Legendary Moonlight Sculptor (Novel)! He flatters people to gain their favor and helps people to gain their loyalty. He'll trick anyone if he gets something out of it, though he does still have some morals. The series is very long.

The Legend of Sun Knight / The Legend of Sun Knight (Novel) - He's the leader of the renowned twelve holy knights, yet he best handles issues "behind the scenes", secretly organizing things so they all fall into place for him later.

How about Houshin Engi? It's a long and completed shounen series with an extremely crafty lead. He always plan ahead, and even if his plans fail, he usually have a plan B or plan C. He is also not afraid to use dirty tricks, so much that sometimes his comrades are ashamed to be on his side.

I know how you feel, just watching how reckless the "do gooders" are makes me skip the scene or cover my eyes lmfao...heres some I think are "decent"...

15: Meisetsu Kougyou Koukou Rugby Bu
666 satan
13
A bat & 2 Balls
Ao No Exorcist (amazing manga & anime)

Hope they're to your liking Peace...

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i like the red paint that comes out when i stab you...

Ao No Exorcist is definitely one of my favorites. I don't really want novels, because I would still like to read manga.

Also, it would be really cool if the protagonist has multiple faces/personalities.

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Nulla in mundo pax sincera
"Always go too far, because that's where you'll find the truth." - Albert Camus

I double recommend The Legend of Sun Knight then; manhua, and in addition to the crafty protagonist, pretty much all of the characters have multiple personalities.

Ageha wo Ou Monotachi - a bit more seinen styled than shounen, and it's just a light comedy, but you may like it.

+1 to this.

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What I like in Trivial Pursuit style. Pick your category:

AIKI dude is anything but dumb, tho u wouldn't know it from first impressions >_>
Random surprise one the breaker: new waves this is surprising as the first one is the total opposite, kid was a fricken moron bursting with power. But now due to reason I won't mention he has way less power and its unstable, so to fight stronger people he has to be craftier during the fights... he's still a bit stupid tho >_>

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Few favs
Comedy:
Kyou kara ore wa!!, Mx0, Angel Densetsu, Skip Beat, Ai Kora, The Devil King is Bored

Romance:
Hana to Akuma, No bra, Shinigami Trilogy, kindan no koi de ikou, Usagi Drop, Threads of Time, Girl Friends

Most under rated:
Kindan no koi de ikou, kyou kara ore wa!.
m0r l83r... maybe >_>

Konjiki no Gash!! might fit

I second (..or third?) these two series!!! They are absolutely great and I could just reread them over and over XD
but I would recomment The Legend of Sun Knight (Novel), since it's a lot better than the manga (IMO)

Gamble Fish - Very crafty male lead.

Gamble Fish looks like a nice read, and I've already read Konjiki no Gash!!.
Mangas like Hunter x Hunter could also work, since Killua is pretty crafty.

________________
Nulla in mundo pax sincera
"Always go too far, because that's where you'll find the truth." - Albert Camus

Bloody Monday?

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Going Kyaaaa!! constantly at Bishounen

Vampire Juujikai
AIKI
Fullmetal Alchemist
Shin Angyo Onshi (manhwa)

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"People don't change, they just give in."<BR><!--url_type_2--><a href='http://webtoons.com/en/fantasy/kubera/list?title_no=83' target='_blank'><u>Kubera is the best.</u></a><!--url_type_2_end--><BR>同人音楽 (doujin music)<BR><!--img--><img src='http://i.imgur.com/CkHPJMM.gif' border='0' alt='Laila Hemawati'><!--img_end-->