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I was under the impression that Halflings in D&D look pretty much like little humans.
But when I browse online concept art and fan art, I see a lot of Halfling images with Elf-like pointy ears... and it isn't always clear which art is canonical and which isn't.
So: In D&D, do Halflings (or some types of Halflings) have pointy ears akin to Elves?
Even if they generally don't, are there exceptions?
If it depends on the D&D version or campaign setting, which ones exactly?
tl;dr Originally halflings were h*bbits (R) straight out of Tolkien, with "slightly pointy ears". D&D had to distance itself from hobbits, with "halflings" like pint-sized humans. Kenders are the first D&D halflings to have really pointy ears.
Though in the Hobbit I don't think the ears of halflings are mentioned, Tolkien did describe them as:
A round, jovial face; ears only slightly pointed and 'elvish'; hair short and curling (brown).
There is very little physical description of hobbits in Chainmail (which just calls them "little chaps" or in Men and Magic (which just refers the reader to Chainmail), but as is well known at the time of OD&D, TSR got into trouble with the Tolkien Estate and had to rename the creatures "halflings".
By the time of the Monster Manual (1977), Halflings are pictured with rounded-ears, looking like small humans, and described so in the first Player's Handbook (1978)
Halflings are very much like small humans, thus their name.
This may have been a deliberate attempt to distinguish D&D "halflings" from Tolkien's "hobbits", taking the literal meaning of "halfling".
In Dragon #85 (1984) there is a short story by Roger E. Moore which first introduces the race of Kender in the person of Tasselhoff Burfoot:
The intruder was barely four feet in height and thinly built; he had bright brown eyes and the face of a ten- year-old human child. Narrow, pointed ears pressed against his light brown hair, which was pulled into a sort of ponytail on top of his head.
This distinction then became established in AD&D 2e, with 'vanilla' halflings continuing to be described as "short, generally plump people, very much like small humans. Their faces are round and broad and often quite florid." (2e PHB), whereas Kender have "distinctive pointed ears that give them an elven appearance." (Monstrous Compendium: Dragonlance)
I don't know the ins and outs after these beginning, but between the de-Tolkienised halflings and the elf-like Kender we have our two sorts of halflings, with Tolkien's original description of hobbits somewhere in between. It seems that Pathfinder chose the Kender-like appearance, though fortunately without the personality traits of those little... (Hang on, where's my purse?)
I know of at least one source that describes halfings as having (slightly) pointed ears: the D&D 3.5e manual Races of the Wild.
Their description ends with:
Their features are more delicate than those of humans, and their ears are elongated and slightly pointed.
My understanding is that halflings in D&D have regular-ish ears whereas halfings in Pathfinder have more sharp ears: this could explain why you're seeing character art of pointy-eared halflings).
This article has pictures of halflings throughout the editions. I notice that all of them (save for the kender) have ears that could be those of a human; that is to say, pretty normal. Especially the 5e halfling: she has very round ears.
Halflings in Pathfinder tend to have sharp and pointy ears. A B C
When I first came across Kender I immediately headcanoned them as Elf Halflings equivalent to Hobbit Halflings in being a smaller offshoot of the parent/cousin race. Since then in my own worldbuilding after first being enamoured of elf-type halflings over human-type halflings because I saw Dwarves as basically also filling the role of a shorter variant of human, I moved on to the idea of the combination of Dwarvish attributes & Elven ones as Tolkien originally indicated ...On the elf side the slightly pointed ears & the nimble agility ...on the Dwarven side the hairy feet, bushy sideburns, solidity, weighing more & being stronger proportionally than size alone warrants aking to strength of Chimps with a somewhat different musculo-skeletal structure, more efficiency, tensile strength. Tolkien rejected idea that Hobbits were a result of Elves & Dwarves interbreeding but to me it seems like a perfectly logical conclusion, especially given that their given origin site as in annals of recorded history puts them right in the borderland between Western Dwarves (Misty Mountains), Eastern Elves (Greenwood) & Men in the north (Eodain/Dale-Esgaroth) & south (Rohan/Gondor). For this explains both the rise of Halflings & the fact that Tolkien marked out three branches of Hobbits.
dungeons-and-dragons-tagged question I'd really like to see an answer that draws from the hoary old days of original TSR halflings (né We's-gonna-get-sued-by-Tolkien hobbits!) to the present day. Illustrations (sourced and credited, of course) preferred. \$\endgroup\$