Just something scratched up together during boredom, nowhere near complete, just throwing it here for other people to add their take to.. Help build on this and let's see how it ends up!
D&D actually had such a class once AFAIK, and obviously other people have had ideas for this as well:
and here's my amateurish draft for one:
D&D Class: Jester or Trickster
A master at deceiving sentient or semi-sentient creatures, often to fatal consequences.
Think a more malevolent (or sarcastic) and offensive version of a Bard (or an exaggerated cross between Bard/Rogue similar to how Paladins can be considered a cross between Fighter/Cleric) but also much more, with a Harlequin kind of vibe.
- Alignment: Any Chaotic
- HD about the same as Rogue/Bards
- Primary Stats: CHA, DEX, INT
- Skill Points just about slightly lower than Rogue
- Class Skills: Balance, Bluff, Concentration, Haggle, Hide, Jump, Listen, Move Silently, Perform, Spot, Tumble
- Expertise in Thrown Weapons. Gains +1 to Attack and Damage with them every 2 Levels.
- Special: Can equip Cards; a new Jester-only Thrown Weapons type with highly-magical effects.
- Weapon Finesse
- Thrown Weapons
- Simple Weapon Proficiency; Dagger
- Sly/Trickery; Jester-only. Taken automatically if CHA 14+
- Unpredictable; requires DEX 14. No one can predict where you will move or what you will do next. Gives a +2 to Attack Rolls and to confirm Critical Hits vs. Lawful targets, and a +1 vs. Neutral targets.
- Sly/Trickery; requires CHA 14. You can fool people with ease and see through their attempts to do the same to you. +2 to Bluff and Haggle Checks, +2 to saves vs. Intimidate.
- Mockery? requires INT 12. You are an expert at concealing Light/Thrown Weapons and Light Armor in the folds of ordinary- and harmless-looking clothing. Gives a +2 to Attack and +1 to AC vs. enemies with less than INT 10
[Choice of?] "Tricks" starting from Level 2:
- Feign Death; Drop to the ground and lay motionless. If you attack any enemy then passing by, you hit them as per usual, but if they fail a [STAT?] Save vs. [#?] + your DEX, you also score an automatic Critical Hit.
- Ruckus; Caper around dancing and throwing vile (and often incomprehensible) insults at foes and friends alike, causing every one within a radius of [#? per #? Level] casting spells or using Skills to make a Concentration Check vs. [#?] + your CHA or fail at whatever they're trying to do.
- Flurry? Requires a Stack of enough Thrown Weapons to be equiped. Shoot 5 Thrown Weapons at once. +2 extra shots every two Levels starting from Level 5 inclusive.
- Switch Sides? Enemies within a radius of [#? per #? Level] must make a [STAT?] Save vs. [#?] + your CHA or believe that you've switched sides to align with them, and stop attacking you. Attacking any of them will [count as a Sneak Attack and?] remove the effect from all enemies.
- Juggle; Requires a Stack of enough Thrown Weapons to be equiped. Enemies AND Allies within a radius of [#? per #? Level] must make a Will Save vs. [#?] + your DEX+CHA or be Mesmerized. Treated as if it were a Spell being cast, with Concentration requirements to keep continuing when under attack. Release Juggle to score an Attack at +2 bonus on all affected Enemies, from closest to furthest, as many as the number of weapons being Juggled. Number of weapons depends on Concentration/2 + DEX bonus.
[Choice of?] Spells gained starting from Level 2; each requires INT 10 + Spell Level
- Expeditious Retreat
Cards - New Weapons Type
A type of Thrown Weapons, only usable by Jesters. Always inflict a very small amount of AC-ignoring magical damage or minor negative effects upon the enemy, for example:
- 1d4 Fire/Cold/Acid damage.
- Slow/Feeblemind/Blind/Stun/Confuse/etc. for 1d4 cumulative seconds on each successful hit.
- Most Cards have a random damage or effect from a certain list.