I've had a few memorable halflings over the years...
Cyralee Brandobaris Arvoreen Perryroyal was a female halfling druid/ranger.
Back in 1st/2nd Ed., there were often a lot of times I went without a steady game for a year or more, so I used to run one for myself - DM-ing and playing the entire party... Since at the time there were still level limits for demihuman characters, I used to play pretty fast and loose with the multiclassing rules, and eventually almost everyone in the party ended up with three or even four classes.
Cyralee was a bit of a beast, to be honest - I'd rolled really good scores for her, and she ended up scoring a lot of nice magic items including a magic bow, and an elven cloak and boots. Given a couple rounds to prepare for a fight, she was absolutely vicious at ambushing enemies, locking them down with spells, and then picking them off one by one before they ever reached the party.
Polly Pureheart, Pint-sized Paladin of Pelor, started out as a joke character...
Polyphemia Peregrine Pureheart is a halfling paladin. Her personality and visual image is straight-up the stereotypical kid's-cartoon "plucky redheaded kid with freckles and a voice like a chipmunk with a head cold"... She has a childlike personality and a child's simplistic black-and-white sense of right and wrong.
When Polly was a little girl in her halfling village every morning she'd walk outside to start her day, stretch and yawn, and then look up into the sky and say, "Hello, Mr. Sun..."
When Polly was still doing it as a teenager, and still retained her childlike personality, everyone assumed that she'd spent too much time staring into the sun and was more than a little bit touched in the head.
What nobody else in the village realized was that, when Polly was six years old, she'd walked outside, looked up and said, "Hello, Mr. Sun..."
And "Mr. Sun" had replied...
Hello, Polly...
Even though I originally made her just for the lulz, I quickly decided that when I got to use her in a game I would play her completely straight - as a study of how someone with a clear-cut black-and-white world view deals with a shades-of-grey world.
And then there's
Ripper...
Ripper started out as a pregen halfling thief I got handed for a game that I jumped in on circa 1990-91 - a bunch of people were playing in my college cafeteria and I stopped to watch, so they told me to pull up another chair and play.
The character had a
ring of jumping and a magical dagger. At one point in the adventure some bad guys had trapped up in a tavern and lit the place on fire with some of their own guys still inside to keep us from escaping. Even though thieves were crap in combat back the, the DM was generous and let me get in a number of backstabs by hiding under the tables... and by using the ring of jumping to leap halfway across the tavern onto a guy's back and cut his throat...
That's when I began to think of him as "Ripper".

Despite having mostly mopped up the guys in the tavern with us there were still a lot more keeping us from escaping the burning building, so I did something unexpected - screaming like a barbarian, Ripper used his ring to jump out one of the windows and charged straight at the bad guys. He'd already tossed some flaming oil out into the street earlier in the fight and using his ring to jump back and forth over the burning oil he managed to stay out of the reach of the bad guys and keep them occupied long enough for the rest of the party to fight their way out.
That fight basically gave birth to what would become Ripper's personality and signature fighting style.
A few years later I got into a 2nd Ed. game, and rolled a high strength... then a high intelligence... and then max Dex. So I decided to ressurect the character. He was now officially called Ripper, and was a fighter/thief -
the largest halfling anyone had ever seen, muscled like a pro wrestler, and often mistaken for a small dwarf at a distance.
He had huge muttonchops and a personality three times his size. He was a charming ladies' man, he drank and swore like a dwarf, he had no problem picking a fight with anyone, and he'd often pass the time singing Orcish drinking songs to the tune of Elvish love ballads and Elven love ballads to the tune of Orcish drinking songs at the top of his lungs. He wrote poetry and spoke six languages. He was also a clever and devious bastard.
I found him a
ring of jumping and some magic daggers as quickly as I could, and making a flying leap onto a target's back with daggers in both hands, wrapping his legs around their chest to hold on and cutting their throat was his signature move.
Rather amusingly, however, one of his first magic items was a set of
gauntlets of ogre power...

People would stare at the sight of a halfling walking down the street with a bastard sword slung over his shoulder and bristling with daggers all over. There weren't any weapon restrictions on backstabbing back then and because he had to wield it two-handed since he was small, he did some
serious damage with it.
Whenever I played him from then on, I always made sure to acquire his
ring and
gauntlets as soon as I could, and always armed him with a ton of daggers and that bastard sword. (Sometimes the DMs I played under would just up and give me those items just to see Ripper in full effect). In one 3.5 game he was fighting an ogre once when I got annoyed at some bad dice rolls. So he dropped the bastard sword and started punching the ogre in the kneecaps until it fell over, then stood on its chest and proceeded to pimpslap it to death. In another, he used the ring to jump off the walkway of a high castle wall, sailing out into midair several stories up and using the momentum to land on a distant guard below, knocking them senseless.
Ripper is basically an in-game manifestation of my id, with almost no superego to overrule his impulses. When I play him, I'm constantly looking for opportunities to let his personality, flair and cleverness generate entertainment for the rest of the party and set up opportunities for them to step into the spotlight.
Back when the
Neverwinter Nights videogame came out for PC, I used to play a female halfling monk whose name I can't remember and wasn't really important - I spent almost an hour just hitting the reroll button on her ability scores until I got nothing lower than a 16, and I freely admit it was solely for the entertainment value of seeing a tiny half-nekid woman beating the hell out of orcs and ogres with her bare hands.

