My favorite weird little guy was a halfling rogue, but he had an academic background. So he played like this overly optimistic nerd who just wanted to make the world a better place. I was playing him in a way that his optimism would fail when facing reality, but I kept rolling 20s. "Couldnt we all just get along?" Solved two conflicts. The best one was, "perhapse you have forgotten the power of love!" Convinced two dragons who hated each other to date. I miss that little guy. I still use his voice sometimes.

My over the top positive lil guy was a halfling bard who was a baker. All his instruments were pots and pans he would bang on. His vicious mockery was telling you ways that you let down people in your life and genuinely wanting to help you do better. His bags were full of homebrewed muffins that were infused with calm emotions which he would use to pacify and bribe NPCs. Whimble Buttercrust became the de facto party leader and turned our resident murder hobo into a struggling pacifist who would snap if anyone put Whimble in danger.

The other halfling in our party was a horny rogue, so I played Whimble asexual. The DM was also horny so they found it amusing to watch Whimble struggling to graciously excuse himself while remaining oblivious (until it was no longer possible and then becoming flustered).