Sin: Hmmm...it's a toss-up between wrath and pride. Often one begets the other in Darkness's case, but I'd say that wrath is closest for the acts of revenge and bloodlust that always lead to something terrible happening to Darkness. So wrath it is.

Virtue: Fortitude. I was going to write that Darkness is defined by his moral code (and hence justice would be the best fit) but that casts him as too much of a religious figure. Darkness's strength is better defined as his unwavering dedication to who and what he must be ('justice' as a virtue implies a choice). His motto (Nescit cedere - "He does not know how to give up") also fits this choice of virtue very well.

Pride - TI's arrogance and self-image both informs his actions and gets him into trouble. He's well aware of his own strength and intelligence and sometimes overshoots it.

Fortitude - If and when TI falters, he wants to do what it takes to re-establish whatever face he lost. He hates being surprised and humiliated and will work to regain control.

I'd say:

Sloth - He'd much rather be sitting on a beach or reading a comic book than training and such.

Hope - He's kind of built around the idea of hope. He's aware he's usually against overwhelming odds, so he just has to hope for things to fall his way.

Dick's major sin is DEFINITELY Gluttony. He's always after the Rocky Road ice cream.

His virtue is Fortitude, albeit misguided. He believes he's Ric Flair and that he can do anything Ric can do. So his Fortitude is due to his delusions.

Sin
For Shadow it's either Gluttony or Wrath as it is mostly those th sins that guide his life. His calm exterior ONLY exist to protect him and those around him from the results of his wrath. On the rare occasions that in is unleashed bad shit happens. With that said I'm going with Gluttony as Shadow never feels he can have quite enough power to offset the evil his bloodline has set loose upon the World

Virtue

This is REAL hard and my answer may make you laugh but at the emd of the day Shadow's virtue is Justice. Few know it but Shadows ultimate goal is to bring a hero to power that can stand up to and defeat villains such as himself. He abhors heroes that suffer from pride whish is why he hates Darkness so much as he sees him as the personification of pride. He wants a perfect hero to bring about perfect justice and until he finds or creates one he will simply enjoy being one of the most evil men on the planet.

Probably a tie between Pride and Envy: It's his pride that gets him into trouble, it's why he does the things he does, stealing the ROH world title. His pride re inforces his actions and gives him excuses to do the things he does, he knows he's good but he won't admit that there are others better than him. He envy's others and that makes him really jealous of the success, he wonders why he doesn't get the accolades and why he isn't as successful as his peers have been and it makes envious and that envy turns into anger which gets him into trouble.

Virtues: I would say fortitude because DeSean never gives up and he never stays down but it's his faith that keeps him going. He's not much of a religious character but it's his faith in God that tells him to keep going and to keep fighting for what he believes in maybe his faith will make him a better person.

The sin is easy -- wrath definitely wins out. Drakus is an angry character who lives to inflict his rage on other people. Although if I could pick two for the character, envy would be a close second, because Drakus' life is miserable and a lot of his rage stems from the fact that he envies those whose lives seem happier or more successful.

As for Drakus' virtue, he's lacking almost all those qualities, but I suppose the one he could plausibly claim is fortitude, otherwise known as courage. In his case, it's really only physical courage though, motivated more by his wrath than a real effort to overcome fear.