A while back, we played a D&D 3.5 game based on having the worst characters possible. We called it the game of suck.

Basic premise: Any time you get to make a choice at character creation, roll randomly. You must accept whatever result you get.

Specifics:

• Abilities: Roll 3d6 six times, assigning the rolls to your STR, DEX, CON, INT, WIS and CHA in order.
• Race: Randomly selected from the entire list of races without level adjustments. (Note: You may need to do some filtering - the list we had was dominated by the ‘artic/desert/jungle…’ races from Unearthed Arcana.)
• Class: Randomly selected from all splatbooks, with the caveat that your class may not match your highest ability score. For example, if your character has high INT, you are not permitted to be a wizard.
• Skill points: Assign each and every skill point randomly between the 45 skills listed in the Player’s Handbook. If you roll a cross-class skill, you have to take it anyway.
• Gaining a new level: Randomise all choices each time you level up. Note it is extremely unlikely you will ever manage to get two levels of the same class.

I believe we took pity at this point and let players pick their own feats, class features, spells, and so on. A truly masochistic group might want to roll these randomly, as well.

EDIT: We were allowed to pick feats from a given book, but the book was rolled randomly from the list of all splatbooks. Great comedy if someone rolls the Book of Vile Darkness.

Playing as sucky characters

I managed to roll up a kobold bard with negative CHA and no ranks in Perform. My total Perform bonus was -2.

I realised fortune had blessed me with a random character strongly resembling Deekin, the annoying kobold bard from Neverwinter Nights. Needless to say, I roleplayed this to the hilt, including the annoying voice (“Deekin greets the noble hero!”) and bad songs (“WE BE IN THE DUNGEON! WOO-YEAH!”)

I won’t say too much more about this game, apart from that CR 1/4th vermin actually posed a significant challenge, and the entire party ended up being killed by a badger bunch of mundane weasels.

*Recommended for a short, one or two session campaign.*