Stout Halfling was obvious – Pinkie is a very homey person with a strong appetite for feasting and partying and quaffing, and that just shouted halfling to me.  
Bard was also a quick conclusion to reach, although I briefly considered trickery cleric and some manner of warlock in service to an endless party. But no. Pinkie is Pinkie, and she Pinkies entirely of her own volition. Glamour Bards are the most fey and wild subclass I could find, so I just went with that.  
Entertainer is just… there was no alternative, frankly.

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…I hadn’t considered that as an option up until this point. I’m definitely going to see if I can figure out a way to make that work mechanically.
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Pinkie isn’t a warlock. Pinkie is the kind of entity who acts as a warlock patron. Consider the Pinkie Promise.