MadWorld/WMG

The Black Baron is Baron Samedi.
... either the deity or the Bond Villain. Either way, it explains how he keeps coming back to life.

Kreese did not actually participate in the Death Watch games.
All boss battles are a fight to the death, and considering that Kreese has supposedly fought quite a number of them and lost, one has to wonder how he survived all of them unless he's just making up some bull.
 * He could just be exaggerating all of his injures and I don't him ever recalled him ever saying that he died, just horribly maimed.
 * Well, he did say he once used an extra life and came back as a roach...

Kreese and the bosses use the balloons.
This would explain how, although it's a fight to the death, Kreese can survive his horrible injures, the bosses can fight you even though Kreese should have killed them, and how the Black Baron keeps coming back.
 * Also, only those who have won a previous Death Watch can use the balloons.

Alternatively, most contestants just think that the balloons are just regular balloons.
Only those who are told by their sponsors or have prior experience in this game know they're extra lives.
 * "It's like they can't even see them!"

The contestants get cloned when they die.
Explains what Kresse says and how the Black Baron comes back.

The Black Baron actually has regenerative powers, and is dangerously masochistic.
Why else would he let his assistant hurt him so dang much?
 * Does this mean The Black Baron is Deadpool? 'Cause that'd be the most awesome thing ever.
 * Alternatively, he makes liberal uses of the Balloons, which Matilda takes advantage of.

The commentators are Statler and Waldorf from The Muppet Show.
After regenerating, of course. Also explains how Kreese survived.

Jack is actually Jack Spicer, Evil Genius...
...on lots of steroids. You see, he built his own arm. It makes sense.

Jack is Jack Thompson
He decided to finally try to outdo all those murder simulators by himself.

Mad World in really an AU G Gundam fan fic
The battles to circumvent wars, the multi-ethnic opponents, the regenerating antagonist that never seems to just die? All things in common. Not to mention the G Gundam commentators never really seem to mind all the crazy stuff that gets pulled.

Mad World is based on future true events, happening due to the insanity of current US politics.
Seriously, it's all coming together. Unleash swine flu and hordes of libertarians on Manhattan, and fly planes into the bridges. Bring in everyone from Sarah Palin to Michael Moore and arm them to the teeth. Pay-per-view on Fox News, with Michael Steele as the host, announcer and deathtrap demonstrator.

Finally, armed with a chainsaw, Jack Thompson treads the blackened streets, ready to put everything he learned from video games to good use.

No, I don't know the meaning of Too Soon.


 * But I know the meaning of Made of Win, good sir, and you are it.
 * You're confusing "sarcastic propaganda" with "win".
 * More like the impression of US politics one gets from being a disinterested (and featherbrained) foreigner who keeps up with them purely for entertainment.
 * Given that the president appears to be a white guy, we can only assume this is what would have happened if John Mccain was elected.

Kreese is actually an unknown alias for Bender Bending Rodriguez
Hence the voice.
 * Another option. He's either Brother Blood or Dr Drakken and he's used his mad science skills to come back from the dead, explaining how he's lost in the Deathwatch games and is still alive somehow.

Kreese is hideously deformed and/or crippled.
Based on the numerous injuries he suppossed to have received. In the future, he will attempt to have his brain transplanted into a robot body, but a mix-up will instead lead to it being placed inside a generic bending unit, the programming of which fuses with Kreese's personality, creating Bender as a gestalt entity.

Onion's aren't Jack's Trademark Favourite Food, but he put them down as that in case he ended up fighting vampires.
He never fought any, despite the whole Castle Dracula zone, so clearly it was an effective deterrent.
 * Except, you know, Elsie.
 * Also, you're thinking Garlic.

Mad World takes place in the same universe as No More Heroes and Killer 7
A crap sack world where the fastest way to get cash is to fight in kill or be killed battles? Cybernetically and biologically augmented assassins? The similarities are obvious.


 * We can all only hope that Jack, Travis Touchdown, and the Smiths never cross paths, or the universe will explode. And it will be AWESOME!

Kreese and Howard aren't the only commentators
Okay, hang with me on this, but in a cutscene, Noa says to cut off Jack's 'feed'. That means there are more than one, which makes sense, considering focusing on one guy in a massive melee would be boring, so all the top-name contenders get their own feeds, with their own broadcasters. Jack's designated duo is Kreese and Howard, all the other competitors of note have two other jackoffs making 'witty' remarks.

When their guy dies, the commentators are either taken off air, or assigned another fighter.

Also, there's a betting pot amongst the broadcasters over who will win, Kreese and Howard just won enough money to buy a metric TON of Scotch! ^_^
 * So, any guessing on who the other commentators are?

The in-stage minibosses are lower-ranking contestants
Tengu, the reaper guy, that Sonic wannabe, maybe even the bull chainsaw and elephant drill guys; all are ranked contestants who've earned the right to fight Jack at his current rank, but of course don't win. They're introduced with relatively little fanfare from your angle because YOU are the boss fight.

Judging by their Recurring Boss status, perhaps they're cloned for later use, or used life balloons as well.
 * Maybe the regular enemies are too

Jack is Hellboy
You will never be able to unsee this.
 * When Jack later died for good, he became Hellboy.

Jude the Dude is Death Blade:
I can't believe I never saw this before. Both use skates, both wear similar ponchos and both are very agile. This is also supported by the fact that Jude is reduced to a skeleton before you kill him. And what is Death Blade? A skeleton, of course. They even have a similar body shape.

The UAA is an imitation of Death Watch
The UAA got all their ideas by watching the games from Death Watch, and considering, they picked it up around modern times. Though the only difference is that they have stricter rules than DW and probably want to keep a lower profile than it. For example, there are no traps or hazards enemies can knocked or thrown into. Also you rank up in the UAA by killing the person 1 rank above you. In Death Watch along as the number is higher than your rank, you challenge that opponent. There is also the fact that DW stations its owned private network for the rich and the powerful watch the games.