A Gypsy is a member of the Romani peoples, a traditionally itinerant ethnic group hailing from the northern subcontinent of India who, for some reason, migrated out into Europe and then America. Long stereotyped as mystics, entertainers, thieves and vagabonds, the term "gypsy" is actually considered racially charged these days. But, in the 80s and 90s, the exoticness of the Romani saw "gypsies" appearing in various /tg/ media.
World of Darkness
In the World of Darkness, there was an actual Gypsy sourcebook released. It is widely considered to be one of the most ridiculously offensive splatbooks that White Wolf ever put out, even compared to the book on Holocaust ghosts for Wraith: The Oblivion (which at least went out of its way to give the actual facts of that particular episode of mass murder and tried to discuss the details in a way that were, if not tasteful, then at least as truthful as the situation allowed).
One of the more minor human subcultures in Warhammer Fantasy are the Strigos, or Strigany; based off of Dracula's gypsy minions in Universal Horror, they are the descendants of a fallen human pre-Sigmar empire that was ruled over by Ushoran, founder of the Strigoi bloodline of Vampire Counts. When Ushoran's empire fell beneath the combined forces of internal treachery and a Waaagh! of Orcs & Goblins, the Strigany scattered and were reduced to itinerant nomads. Persecuted and oppressed by the Empire, they ultimately reacted by turning to the powers of darkness; many became warlocks and necromancers, and many more actively sought out the ghoulish bloodline that had once protected them and placed themselves back under their protection.
Dungeons & Dragons
Being based off of Universal/Hammer Horror Films, where the "gypsy seer/mystic/thug" was a stock character, Ravenloft is naturally home to the Vistani, a race of eerie, magical gypsies who are treated as being an entirely different species of creature to humans - that's why you can only play their Half-Vistani offspring. In the days of Advanced Dungeons & Dragons, it was also home to the Gypsy class, a rogue sublass that was added to the register of thief and bard in "Domains of Dread".
Gyspies feature in The Forest Oracle, AKA the worst module TSR ever published. There they serve as a bizzare and badly designed tacked on final encounter to the already bizzare and badly executed module. They want the PCs to rescue their Pegasus (how they got it is never explained) from an Ogre that has a golem capable of discerning gypsies (how he got it is never explained) and mind control the PCs into doing it, no save, without reward if they refuse (how they got this ability is never explained).
Spelljammer is home to the Aperusa, who seem to be literally every bad stereotype of gypsies as traveling thieves and con-artists turned up a few notches. To avoid the mistakes of Ravenloft, the Aperusa are presented as a human culture within Wildspace, not their own distinct race; as such, players could even be aperusa themselves, with aperusa being handled as one of the kits in The Complete Spacefarer's Handbook
Golarion is home to the Varisian culture, of which one sub-culture has rather gypsy-like traits.
In general, the existence of the gypsies of D&D is something of an old shame; Wizards of the Coast does its best to ignore them, and even the Vistani are a complicated mess.
The Gypsy class in Advanced Dungeons & Dragons is a Rogue family class introduced in Ravenloft: Domains of Dread. Its primary Ability Scores are Dexterity and Charisma, and it requires a minimum score of 13 for Constitution, Intelligence and Wisdom, as well as a minimum score of 15 in Charisma. A gypsy gets a +10% bonus to experience points if it has 16s or more for both Dexterity and Charisma. It is open to the Human, Half-Elf and Half-Vistani races.
Gypsies are effectively a Ravenloft-appropriate replacement for Bards. They don't get access to thief skills, but they do gain some increased sagely knowledge and limited spellcasting. Restricted to Lawful and Neutral alignments, gypsies cannot use ANY metal armor - not even elven chainmail, the usual "get-around" for this restriction - nor can they use shields. They can only use one-handed melee weapons, but can use two-handed missile weapons. Unlike thieves, gypsies don't gain the ability to use clerical and wizardly spell scrolls at 10th level; instead, they can use any magic item that is either thief-allowed or which emulates spells of the Divination school, and can learn Divination school Wizard spells of up to 4th level. Gypsy spells don't need to be memorized ahead of time (a prototype of the sorcerer), but they always have a casting time of 3 turns; gypsies use a ritual magic rather than the active combat spells of the wizard.
For other unique class features, gypsies have the traits Gypsy Clans, Knife-Fighting, Gypsy Lore and Sinister Perceptions.
Gypsy Clans is one of those awkward "rollplay to roleplay" class features that proliferated in AD&D. Basically, it gives the gypsy PC different reactions to gypsy NPCs depending on how closely their alignments match.
Knife Fighting gives the gypsy an advanced affinity in dagger-wielding. Gypsies can specialize in the use of a knife, just like a fighter, but not as effectively; they gain a +1 attack bonus and a +2 damage bonus, but they don't gain any extra attacks.
Gypsy Lore gives the gypsy a 5% chance per level to know something relevant, if sparse, when confronted with anything of interest. For example, a 12th level gypsy has a 60% chance of knowing something useful about a magical item or a Darklord that the party encounters.
Finally, Sinister Perceptions is another "rollplay to roleplay" class feature; when interacting with non-gypsies, all reaction rolls are immediately shifted 1 step towards Hostile. Oh, and for added bullshit, a gypsy's initial reaction and loyalty base bonuses count as penalties when interacting with Vistani, as the "true gypsies" of the Demiplane of Dread look down on mere mortal nomads.
One of the more... embarrassing... kits to come out of AD&D, the Gypsy-Bard is presented as a nomadic entertainer with distinctly unconventional views on property - namely, they recognize property as belonging to someone only so long as it is held or being used, and don't recognize the concept of the land as "private property". No, seriously - take a look at this flavor text from The Complete Bard's Handbook and you can see the kind of bullshit this class was saddled with:
I'm known as Madraime, and I'm a Gypsy lady. Oh, I'm not what most people would call a typical Gypsy. Within the society of gypsies, there are many different types of individuals. I am what is known as a Gypsy-bard, performing-Gypsy, or dancing-girl.
I travel with my father's caravan, performing for the locals of a region as we pass through. When I'm not singing and dancing for the outsiders, I often entertain those of my caravan in the evening hours. There is nothing as lovely as spending an evening among my own kind, dancing, singing, and enjoying the company of those who understand the world.
Like all Gypsies, I realize that humans, elves, dwarves, and others were meant to lead lives of inner discovery, peaceful joy, and association with nature. I know that many people distrust Gypsies, calling us thieves and worse. This occurs because we Gypsies are misunderstood. Our beliefs are so pure and so natural that they are hard for outsiders to understand.
For example, as a Gypsy, I understand that ownership of an item exists only so long as the item is not ignored or forgotten. If I lay down my magical dagger, walk away, and one of my brothers should find it, the dagger is then his. If I want it back I must trade him something in exchange.
How can anyone claim to own something that they aren't using or aren't holding? What gives a king the right to say that he owns the land of a country? The land was there before he or his family ever lived, and it will be there long after they are all dead. Likewise, how can a farmer claim that he owns the sheep that feed upon the land? These sheep exist because they eat the fruit of the land, and the land belongs to no one. The ways of outsiders are very odd indeed.
We Gypsies are a peaceful folk who wish only to travel upon the good earth, laugh, sing, and live the ways of life.
Cringing yet? It gets worse; from that introductory flavor text, the kit description goes on to include the following statements to define the "philosophy of gypsy life":
- Gypsy-bards are free thinkers. For example, many do not marry, seeking companionship only for as long as both parties agree to the arrangement.
Gypsy-bards love nature.
- Many Gypsy-bards don't worship deities (although certain deities may look over them). Instead, they worship the concepts of nature, free will, and life.
- Gypsy-bards draw their energies from their free will, their brethren, and from their natural surroundings.
- A Gypsy-bard is loyal to and protects his friends, but friendship must be earned, and it is not gained easily.
- Possession and ownership are the same.
- Money is useless unless it brings you pleasure; trade is a better form of commerce.
- You should always dress and act naturally and comfortably.
- The rigid customs and beliefs of non- Gypsies are foolish and should be ignored.
Mechanically, the gypsy-bard is a bardic kit that specializes in Dance, Musical Instruments and Song as its performance-mediums. It cannot be Lawful Neutral in alignment, and alongside humans, elves can take this version of the bard class, reaching up to 9th level in it. A gypsy-bard's secondary skills are: Forester, Gambler, Groom, Hunter, Jewelr, Teamster/Freighter, Trader/Barterer. It must take the dagger/knife as its first weapon proficiency, and its first sword proficiency must be either khopesh or scimitar. A gypsy-bard canot become proficient in the use of battle-axes, lances, polearms, tridents, two-handed swords, bastard swords, or warhammers. They can only wear leather, padded, studded leather, or elven chain mail for armor. Nonweapon proficiencies associated with the kit are: Dancing, Direction Sense, Languages (Modern-Gypsy), Musical Instrument (tambourine, violin, mandolin), Ancient History, Astrology, Cooking, Craft Instrument, Disguise, Fire-Building, Gaming, Herbalism, Hunting, Juggling, Singing, Spellcraft, Survival, Tracking, Ventriloquism, Weather Sense.
- Animal Rapport: A gypsy-bard automatically gains the proficiencies Animal Handling, Animal Lore, Animal Training, and Riding (Land-Based), with training and riding skills extending to any animal with which they become familiar. At 5th level, a gypsy-bard can cast Animal Friendship at will by speaking to animals in the secret gypsy language. At 10th level, they can cast Locate Animals or Plants at will. At 15th level, they can Speak With Animals at will.
- Allure of the Gypsies: If a gypsy-bard performs before a willingly participating audience (or 3+ gypsy-bards perform before any audience) for 1d10 turns, they can mimic the effect of one Enchantment spell that they have in their spell-book by rolling a successful "Chance to Learn Spell" check. The range, duration and other effects are based on the level of the performer "donating" the spell.
- Fortune Telling: If a 5th level or higher gypsy-bard has access to any Divination-based magical item, or a Deck of Many Things, they can use that item as a focus to perform an augury spell. This "scrying" can be done 1/day per five levels, allowing them to ask one yes/no question per five levels during that day. A gypsy-bard does not have to be able to actually use the "normal" effects of that magic item when using it as a focus, and using it as a focus doesn't trigger its normal powers, such as the effects of drawing a card from the Deck of Many Things.
- Psionics: All gypsy-bards should be Wild Talent psionicists, if your campaign uses those rules.
Special Hindrances: Gypsy-bards suffer a -25% penalty to their Climb Walls skill when climbing cliffs, building walls and cave walls - they're specialized in climbing trees.
Apart from these traits, gypsy-bards have the same requirements and class features as a standard bard.