"I'z da biggest. So I'z da boss."
- -The Orks' simple yet highly effective method of determining who's in charge.
A Warboss is the biggest, baddest, meanest and greenest ork in a tribe, and the second-biggest possible type of ork within the species - the biggest being the Warlord. These guys have been through a hell of a lot of fights, and the respect and submission that their tribe shows for their prowess has caused them to reach gargantuan size (a warboss easily towers over a space marine and is capable of reaching the size of a Dreadnought if he fights and wins enough). Because the Orks grow in proportion to how much fights they've won (getting beaten doesn't count!) in their lives; a tribe's warboss size alone proves how 'ard and killy he is to everyone else, both to fellow Orks and the enemy. If that isn't enough, the other ways of showing off their rap sheet is through the use of boss poles (spiked poles that contain the impaled heads of the warboss' fiercest opponents) and the biggest and flashiest gubbinz the meks can give to the boss; like dead 'ard cybork armor, the shootiest shootas, the choppiest choppas, and/or the Orkiest wagons.
A Warboss is what you get when a Nob rises through the ranks of the tribe through either cunning brutality or brutal cunning (or a mixture of both), eventually making a power play against the reigning Warboss and nabbing his spot (and all the shiny gubbinz that come with it.) Sometimes this turns out differently, with the Warboss dying in a genuine scrap with the enemy while his Nobz all fight amongst themselves for the right to take his place.
A Warboss leads from the front, eager to have the chance to add some heads to his pole. Don't think they do this lightly, though - Warbosses are always keen to slap about the Meks of the tribe to make them give them the shiniest bitz. Despite their pretty much single-minded focus on warfare, they often end up gearing up completely differently than one another based on preference and clan. This just as often results in the already ridiculously huge bastards having Mega Armour or something welded to them as it does having a bitchin' bike to chop heads off from at high speeds.
Warlords are the biggest of the big - so big that they can command many tribes under their flag into one big Waaagh! These are the most exceptional individuals of the orkoid race, as one would expect from an ork so big he can boss other Warbosses around.
The Warboss of a Freebooter group is called a Kaptin.
On the Tabletop
The Warboss has always been, and will remain, one of the most iconic and generally useful HQs to the Orks, and maybe in the entire game. They haven't got the resilience of armour that Marines have, the sheer killyness of a Chaos Lord or the supportive abilities of a Farseer or a Tau Commander, but make up for it by being resilient, killy and supportive at the same time, while being pretty damn cheap for what they do. Let's dive in, shall we?
In terms of stats, the Warboss is in a good spot, having WS 2+ T 5 S 5 A 4 and three Wounds, making him quite a powerful git off the bat. He also has a Ld of 9, alongside Scrap Armour, giving him a paltry 4+ Save. This might seem a bit lousy for such a prominent and powerful character in a WAAAGH, but that doesn't account for his upgrades, which severely boost him and make him into a true force to be reckoned with.
You start out with a Choppa and Kustom Shoota, and frankly, that isn't all that bad a choice. Sure, it doesn't do much that other units in the Codex can't, but that's not the point - It allows you to put a cheap Warboss in a large Mob of Boyz and boost their melee output, while helping with Ld and being able to fully utilize his most important supportive ability, which we'll touch upon later. You can, however, switch it for a Big Choppa, which will make him S 7. The Power Klaw - which is right 'ard and a great choice always - is the most powerful melee option simply for doing plasma-to-Railgun-like damage with the same AP properties in melee combat, however, it's also unwieldy which will allow many opponents to hurt or even kill him before he makes his attacks.
For shootin', you get a Slugga of the bat, which is pretty alright for the most part - Warbosses aren't really ranged models. If you pick a Specialist Weapon or a Two-handed one, however, feel free to grab a Shoota for a bit more shootin', if you so desire, or maybe a Kombi-weapon, the Kombi-Skorcha being one of this author's favorites.
Defensively, there's not much of a choice for a Warboss - He tends to use Boyz or Nobs to defend him through LoS checks. It's still pretty mandatory to pick a cheap 'Ard Armour for a 4+, so you'll get a save against Bolters at the very least. You can also really pay up and get a Mega Armour, which is like a Terminator Armour, but without 5++ and with Slow and Purposeful. This is generally a great choice no matter what, though expensive.
On top of this, Warbosses have a multitude of gear to choose from, one of the most notable being a Warbike, which'll make a right 'ard and fast model to put in a right 'ard squad of fast models (the infamous Nob Biker Star includes this). You can also go with a Bosspole, which is great if sitting in a large Mob, or the ever-so-awesome WAAAGH-banner, which boosts your unit's WS by one point, which will be felt when charging other WS 4 units (if you are in a Nob unit, pick another Nob to have it, since it'll make the Warboss less of a target). There's also the Squig Hound, which is a free re-roll on one attack for almost nothing, Cybork Body for 6+ FNP, Gitfinda for BS +1 when standing still (Which Warbosses shouldn't really do) and Ammo Runts, for one free re-roll of a shooting attack for each runt.
And after all that, there's the Gifts of Gork and Mork, which, for the most part, are pretty nice. Standing out is Da Lucky Stikk, the late Makari's banner, which will allow the Warboss to re-roll any and all failed Armour, Invulnerability and to Wound, but if you ever roll three 1's with these re-rolls, your Warboss goes, no questions asked. Other great choices are Da Finkin' Cap, which boosts your Warboss' tactical support immensely, though sporadically, and Da Ded Shiny Shoota, which hits your own units when it misses.
The Squiggoth in the room is, of course, the WAAAGH Ability. Once per game, the Warboss can call a WAAAGH, which allows all units in your army with the 'Ere We Go rule (which is pretty much every fucking unit in the entire Codex) to run AND charge in the same turn. This is what make melee Ork lists possible, as it can make your mobs touch enemy units at Turn 2, at which point a good chunk of your army will be doing bisections in an expedient and efficient way. It will also make your enemy react and play to your actions, which is funny as hell, when people assume they can just blow away the horde for lulz. This is also what makes Warbosses your supportive HQ, as, alongside some defensive options, Da Finkin' Cap and proper use of the WAAAGH, the Warboss, costing round about 100 points, boosts your army to extreme levels that no other HQ can help you with.
Big Meks do defense, shooting and weird gadgets, the Painboy tarpits and the Weirdboy psyking up the enemy, but the Warboss is the duct tape, gum and liberal kicking that makes this sporadic and rowdy band of lunatics into an efficient and scary monster for any enemy to face. Unless it's Eldar or Tau. Then nothing can help you.
In 8th Edition, WAAAGH is modified (It is also now called "Waaagh." Apparently Geedubs doesn't know about the shift key.) Instead of once-or-twice-per-game shenanigans, any Ork Infantry unit within 6" of the Warboss can advance and charge. If you position right, you can probably have 3 units of 30 Boyz all running across the board at around 8 inches a turn for no penalty except shooting (which, to be fair, isn't much of a problem.) He also now boasts 2x the amount of wounds he had in 7th edition, and In general is a lot more affordable. The Squig Hound now simply give the boss 2 2+ Strength 3 attacks for 0 points, so the only reason to not take it is... there isn't really a reason. Bonus Points if the Squig Hound gets the finishing blow on the enemy Warlord. Plus, with Initiative gone, he can now actually hit first, and with a power claw he'll be shoving 4 3+ Str 12 Ap -3 D3 wounds down the enemies throats before they get to react. He also now has a 4+ save, as well as an extra point of strength. All for an even lower price (though it depends on how points translate through editions.) With a Power Klaw (which you should have in 95% of all situations) he comes out to 88 points.
The Warboss appears as the secondary commander for the Orkz in the original Dawn of War. Most factions start with their army's commander, but the in game fluff says that the Warboss only joins battles that he considers big enough to be worth his time. Hence you need to tech up to get him.
The Warboss has the most health of any hero next to the Daemon Prince and Necron Lord with the upgrades added in Soulstorm, but falls short compared to the like of the Force Commander and Chaos Lord in terms of raw damage since his abilities are more aimed at buffing large groups of Orks than himself.
In Dawn of War II the Warboss is one of three heroes the Orks can pick before the game begins, serving as their offensive hero. If you want to play an Orky style with a focus on melee, the Warboss is your Ork, because his global abilities are designed for melee. "Use Yer Choppas" increases melee damage, and melee skill giving a higher chance for special attacks to knock back an enemy. His other "Ard Boyz" cuts melee damage in half. Early game he's one of the strongest heroes in a direct fight and can knock down squads with is Stomp ability. Whether or not you want to focus on the wargear to bring him to his full killing power depends on the situation.
Most commonly you will see a Warboss given a Power Klaw since it does the most damage and packs a punch against vehicles. His best bet for armor is usually "Eavy Armor for the health boost, unless fighting Tyranids or other Orks, where his Spiky Armor that deals damage to enemies every time he's hit in melee, becomes a viable choice. His accessories have two good for what he does, the Boss Pole increased health and suppression resistance within its radius (this includes the Warboss), and the Trophy Rack which decreases enemy damage. Which is better depends on the situation, the boss pole is more likely to be helpful in a team game with more friendlies to affect, especially if you want to stack it with ally buffs.