Well lets face it unless Tasky appears in Avengers as an enemy (unlikely given the caliber of enemy they are going for there) or in Deadpool as an enemy (would be likely if Deadpool wasn't stuck in production limbo) he isn't going to have a big screen appearance which is a shame really because as both a hero and a villain he could turn out a very good film if given the chance. So here's how I would do it:
Now I like Taskmaster's original costume. I think the skull-mask, cape etc.... are all awesome....In the comic world!!! When it comes to costumes some of them just don't work on the big screen. They look poorly put together or sometimes downright weird. For example I found Captain America's suit in the Avengers a bit stupid really.
So as much as i'd like to see the original Taskmaster suit I have a feeling that it would be one of those suits that just wouldn't work on screen. However that isn't Tasky's only suit we have the one that was given to us by UDON which was brilliant and has that modern techy feel about it. Another reason I would favor UDON's suit here is because of the gadgets Taskmaster had with it. The image inducer for example is something a top tier assassin should have to slip around unnoticed or the weapons generator that allowed him to copy other people's fighting equipment (Spider-man's webs, Wolverine's claws, Cap's shield etc...). Whether they copy UDON's design exactly (unlikely as movies always like to do their own thing) or not it should definitely be the basis for his suit.
As I said before one of the great things about Taskmaster is he walks that grey line between good and evil. Thus you have a lot of room to play with him character wise. One problem is fitting him into the Marvel timeline as we already have the Avengers and other Marvel-verse movies so establishing a timeline is key. There are multiple ways of creating a plot for Taskmaster this is just my idea for it:
The whole movie takes place a few years before the Avengers before movies like Iron Man, Thor etc.... Nick Fury has just become head of SHIELD and of course to prove he is up to the challenge wants to make his mark. HYDRA as we saw in Captain America the first Avenger is actually still operating under the radar in modern times but has evolved beyond a simple R&D department into a fully fledged terrorist organization. Fury decides that HYDRA must be dealt with and sends in his best agent and current SHIELD drill master at the time Tony Masters. His task is to infiltrate HYDRA and feed information back to SHIELD. Before however Masters agrees to undergo a procedure designed to increase his memory, cognitive functions and give him an eidetic memory. This would mean that he would be able to remember anything he saw in HYDRA without the need to steal files and risk discovery.
Months after he is posted in HYDRA things start to go wrong. The expansion of his mind allowed him to retain huge amounts of information however gradually he starts losing the rest of his memories as the vast amounts of information he stored from HYDRA overwrites everything else until one day he wakes up with no memory of SHIELD at all and believe's himself to be a HYDRA agent. So of course doesn't feed Fury anymore information. Fury assumes when Taskmaster stops making contact that he was compromised and killed. Due to his ability to instantly remember anything he see's (including fighting styles) Masters is chosen by the current head of HYDRA, Kraken to train HYDRA agents including his adoptive daughter Viper and is given the UDON style stealth suit and gadgets as a gift for his services. After a while Kraken notices that SHIELD has somehow gained information on HYDRA due to SHIELD agents appearing at key points in HYDRA business transactions and assign's Taskmaster to find out who the leak is and plug it. During his digging Taskmaster comes across a video surveillance tape that had been modified in such a slight way that anyone but him would probably have missed it. He manages to pull up the original surveillance tape and is horrified to see himself breaking into HYDRA security systems and stealing information with the use of a flash drive and hiding it in his quarters (when the video was taken Masters was panicking as he realized he was losing his memory and knew the only sure way of keeping the information was to store it somewhere other than his head. His panic was what caused him to poorly edit the video).
Unfortunately for Taskmaster as he hadn't been expecting to see himself there he'd played the video in the presence of Kraken and other HYDRA members. Of course they quickly turn on him and Taskmaster is forced to fight his way out just before stopping by his quarters and taking the flash drive with him. SHIELD however had been keeping tabs on HYDRA bases mainly due to Fury's guilt at getting Tony killed. As Taskmaster flees the HYDRA base a SHIELD agent's scanner picks up the flash drive as a piece of SHIELD technology. Upon informing Fury that someone just came out of HYDRA with a piece of SHIELD tech he sends a squad of agents after Taskmaster (of course due to the suit Nick doesn't recognize him as Masters). Both HYDRA and SHIELD then proceed to hunt down Taskmaster. HYDRA to kill him for his betrayal and retrieve the information on the flash drive and SHIELD to obtain the piece of tech they know was Master's and most likely has more HYDRA information on it. During the course of the film he gradually begins to remember who he is as he breaks into the flash drive and seeing the information stored there. When Fury realizes that his agents are failing to recover the drive he sends in his two new best operatives to hunt down Taskmaster. Black Widow and Hawkeye.
By now Taskmaster is fed up of people trying to kill him and lures both HYDRA and SHIELD into one area (heck you be clever and make that place somewhere in Budapest to match the quote from the Avengers about Black Widow and Hawkeye having a lot of trouble there). Which breaks out into a fight. The black and white video we see in The Avengers movie of Black Widow and Hawkeye fighting side by side could have been taken during this battle as we don't see who is shooting at them (another good way to tie in the Avengers). During the chaos of the fight Taskmaster tracks down Kraken and kills him knowing that is the only way to get HYDRA to leave him alone.
After the fight only Taskmaster, Black Widow and Hawkeye are left standing and the duo attack Taskmaster not knowing who he is. During the fight Black Widow see's how he predicts their every movement and that he knows exactly how she fights. This leads to a flashback and she realizes who he is as Black Widow was just an initiate before Taskmaster disappeared and he had been the drill master at SHIELD at the time thus Taskmaster had been her trainer after Barton had brought her into SHIELD. Realizing this is why they aren't beating Taskmaster she stops the fight just as more SHIELD agents arrive. Now knowing exactly who he is Taskmaster gives Fury the flash drive but still holding a grudge against Fury for just leaving him for dead says he wants nothing more to with SHIELD. The film ends with Taskmaster becoming a mercenary and Viper now the new head of HYDRA is seen over Kraken's dead body vowing to find Taskmaster and kill him for betraying them.
The part about how Taskmaster gained his powers and about him being a SHIELD agent is only revealed nearer the end of the film so that through the whole thing you are basically in the same boat as Taskmaster. Two agencies are hunting him and you have no idea whats going on until later on where it pieces together. This is of course a very very basic outline and there are so many other ways this could be done.
Director: There's only one person who can direct a film about an amnesiac killer and make it stunning and thats Paul Greengrass the director of The Bourne Supremacy and Ultimatum. I can see a Marvel/Bourne hybrid looking absolutely awesome. Greengrass knows how to deal with characters exactly like this!
Stunt/Fight Choreographer: Nicholas Powell. He was the fight choreographer for the Bourne Identity and won best fight choreography for it. He has also won multiple other awards in this are for different films. Some of his work includes: Push, War, 28 Days Later and the Last Samurai. My hope is that he would give Taskmaster the brutal efficiency in hand to hand he is known for.
Fury, Black Widow and Hawkeye can all be reprised by the actors that were in The Avengers.
Taskmaster: Matt Mullins
I'm a big fan of taking largely unknown actors and giving them a shot. I think Mullins would do a good job as Taskmaster. Reason one is because ontop of being an actor he is a very good martial artist. Another is because of when I saw him in Blood and Bone. The character he played in that (Price) resonated cockyness and suaveness which is exactly how Taskmaster acts in his confrontations. I watched that scene again and I could see him pulling of Taskmasters fighting style and personality brilliantly. For those of you who haven't seen it here is the scene I was referring too:
Kraken: Liam Neeson
Neeson has experience in playing comic book bad-guys in charge of a lot of men *cough*Batman*cough* he also has quite a bit of experience with fighting and action scenes he would play Kraken well in my opinion.
Viper: Diane Kruger
I think she would do a good job as Viper you'll have to imagine her with her hair dyed green lol. She's a pretty solid all round actress.
This was just my take on what route they should take. What I said earlier basically summed it up a Marvel/Bourne hybrid. A Taskmaster stand alone movie is most likely never ever going to happen even though people have expressed interest in the past: http://www.superherohype.com/news/articles/102138-exclusive-joe-carnahan-on-taskmaster-and-preacher I'm just hoping Marvel doesn't fall into the trap only using characters like Iron Man, Thor etc... because there are so many other characters out there that would make great movies an yet they are pushed to one-side in favor of the big guns.
So in a sense while I have used Taskmaster as the example here, this post is mainly about how other lesser known characters if given the chance are just as interesting as the more mainstream ones. However Marvel have been a lot more supple than DC in this area so if any company is going to make a film of one of their lesser known characters I would put my money on them. Not to mention it gives you an opportunity to pad out the universe by including other characters such as Black Widow, Nick Fury etc... and giving more information on how they got where they are today. Anyway this had just been rolling around my head for a bit so I decided to put it out there.