James Gandolfini was a perfect casting choice for the Kingpin, now whether or not he'd do a Netflix show is a whole nother thing. The casting suggestion in this article are based on 3 criteria, baldness (which usually also includes some solid actors) Acting chops (most of which are bald) and bigness (Because they could always shave their heads. But as I said without a big, bald, big name actor (who also would consider a Netflix show) there isn't a perfect casting. Remember the Kingpin will likely be a lynchpin character for all of the netflix shows, Daredevil, Luke Cage, Iron Fist, and Jessica Jones. He needs to be a strong actor and be mennacing physically especially if the casting for Luke Cage turns out to be someone like Dwayne Johnson or Chad L. Coleman who are really big guys on their own. The Kingpin has to be bigger.
Bigness:
My First suggestion if we're going for Bigness is Conan Stevens. He would have a british accent so the character biography would need tweaking, and he'd have to shave his head. But unlike the other truly huge actors in Hollywood (He's over 7 feet tall strong and big) He can act. Now I don't know if he is on the level of some of these other character actors, but in Game of Thrones as Gregor Clegane (The Mountain) and in the Hobbit he showed that he can be truly frightening. The Issue though is that his actual acting ability is in question. Can he move the film forward.
The other Actor based on pure bigness is
Kristian Nairn. If he shaved his head and beard physically he would be perfect for the Kingpin. But I believe that's where his similarities stop. As Hodor he plays the gentle Giant. He would be perfect for Of Mice and Men as Lenny but he doesn't strike me as menacing or violent. He'd also be a British Kingpin and I don't know if he can act. On the one hand he and Stevens are ideal in celebrity level to take on the character in a Netflix show but for a character that would need to be played flawlessly it doesn't seem as though he'd be the ideal actor at all.
Baldness:
We know
Terry O'Quinn can act. That's not a question. The biggest things that people will have a problem with in this casting is his age and size. He could easily play a violent, but brilliant villain. But he needs to be seen a physical opponent for the Daredevil and Luke Cage in combat right? If this is a major issue there could be some CGI manipulation but considering The direction Marvel wants to go, if Terry O'Quinn was cast they would likely use the Kingpin as a behind the scenes villain and never use him as a combat villain in order to excentuate his age and lack of ideal size for the villain. I think O'Quinn is one of the most underated actors in hollywood and would jump at a chance to show off as a major villain in the series but I believe he's better suited for the roll of Orson Randall in Iron Fist than any other character in the series.
Michael Chiklis can act. In the Shield he showed he can be menacing, violent, and intelligent. His accent and maneurism make him ideal for the Kingpin. Chiklis would likely also be willing to do a Netflix show. The biggest obstacle for him is his size as well. He would need to be a foot taller to truly fill the "shoes" of Wilson Fisk. With Chiklis though I feel like using camera angles and some CGI you could make him big and it could look natural. Not 7'0 tall big but big enough that he would seem like a close fight with a possibly more slight Daredevil.
Acting Ability:
Rory Mccann can act, and he's scary, he's going bald so I'm sure he'd be willing to shave his head. He's violent and large enough to be a menacing enemy for a large Luke Cage actor or a slight build martial artist. He's also of the perfect celebrity calibre to be willing to do a Netflix show. He's another Game of Thrones' actor but unlike the actor that plays his brother he actually has lines. He's not the size of "The Mountain" but he's still not at all a small or slight man. As the Kingpin his age and Acting skill would fill every requirement, the only issue is the characters origin would need to change. Instead of the mean streets of Brooklyn he's have to be from Glasgow. A Scottish accent is hard to cover up.
When the original Idea of a Daredevil movie was bounced around in the early 90s the obvious choice for Kingpin was
John Goodman. He's a very big and physical actor who has played frightening before. In the realms of Hollywood John Goodman is seen as one of the finest US actors alive. Though he hasn't won as many awards and his celebrity doesn't always reach the levels of others he has been amazing in the past. He could definitely carry his acting skills to Wilson Fisk. Every character background and nuance would be well portrayed by Goodman. The biggest issue is age and physical skill. He's not athletic, or young enough to do the fight scenes and he wouldn't be a believable physical challenge for a young fit actor to defeat. The character would have to be more like the character described for Terry O'Quinn the manipulator behind the scenes. Not the one that fights and defeats Murdoch in combat.
If we're going to go with an actor just because he's a good enough actor to swing it, who'd definitely be willing to play the part of the Kingpin,
Bradley Whitford might be the most likely casting. He has 3 major things going for him. Though he's not big or bald, he can do stunts as seen in the Good Guys, he is willing to get larger for a roll. He's not too old for the physical stuff, he's worked with series producer Drew Goddard before and he has been quoted as a fan of Whitworth, Whitworth is the exact level of celebrity that he would be willing to do a long running Netflix series. The 2 major reasons why I don't think he'd get the roll, the Peggy Carter 1 shot where he played a Shield agent, the Marvel comic universe like's their continuity, even if 90% of people didn't see it it could confuse people, and 2 he's too physically small. The small issue could be covered up with angles and CGI but if they do move more toward making the Kingpin a behind the scenes manipulator over a in the street action villain Whitford would be well suited to the roll.
These are some of my ideas. I feel like the lynch pins of the shows will be the reoccurring villains that we will see in every series, Kingpin, Hammerhead, and Hopefully Vulture would need to be just a few of these.