Random weirdos in a tavern?

Colville suggests that starting in a tavern is a chance to show off the setting in a microcosm. Put folks there that represent various factions or attitudes prevalent in the setting. When I ran a Savage Pathfinder game and had my players start in a tavern, I had some incurious off-duty town guards, the dillettante son of the mayor. I couldn't figure out a way to work in the diabolist church (I set my game in Cheliax), but I did have a choice of several "first jobs" for them to take.

This looks fun ! Here is my try:

• a emaciated monk in a corner of the tavern, who scrutinize every patron and have incendiary arguments with anyone trying to eat anything (drinking booze leave him unfazed). Call him Brother Leffe !
• a table of 4 card players which include a very small dwarf. The dwarf can't see the others well (his eyes are barely at table level), loses a lot of gold, and can't stop playing until he wins. The others are cheating quite openly.
• a hulking half-orc, laden with scars and equipped for war, chugging pinchers after pinchers of milk. Afraid of drinking alcohol.
• a farmer with his 2 elder sons sitting with their cow at a table. It is their only chance of earning money this season and will not leave the cattle any minute. They will get violent if anyone gets too closed to the cow.
• a pointy hat magician seems to have a telepathic discussion with a cat sitting on its table. He looks turn by turn surprised, inconvenienced, worried, anyway it looks like the cat is leading the talks at its disadvantage.

Use this as an opportunity to set the tone for your campaign and introduce the players to the world. What sort of races/professions/attitudes are common? Have your initial NPCs representing them.

A running gag of my campaigns is that they all start in a tavern (or bar, or mess hall, whatever fits the setting).
The barkeep is always an orc (in a modern setting I'd describe him as incredibly tall, muscular man, with a sickly skin tone, etc.) who wipes down the used beer mugs with his apron and puts them back on the shelf.

As usual, don't forget to discuss plot hooks in session zero, and make sure that the PC have an in game reason to work together. We all have heard the horror story about the party of a chaotic evil, a lawful good hating each other while the stict neutral robber has a not my problem attitude which basically makes the whole game a hell.

Knowing how player behave, I would expect that some of these "weirdoes"will be recurring NPC. Some thoughts though

• Just a couple of locals, you know the farmer complaining that there was too much/not enough rain, the other ones thinking that adventurer are crazy and badluck, the tavern maid who wish to marry a rich adventurer to get out of that shitty town, the farmboy who dreams of becoming an adventurer.
• The recruiting sergent escorting a couple of young enlisted to the next-town, and trying to find some others, it's a great way to tell A war is ongoing
• The travelling merchant with tons of wonders, tales from the town, and potentially a recuring NPC
• The doom prophet, like the half-crazy priest who comes to the town to talk about a great evil coming (a Great way to tell something bad is awaking)
• If the campaign is more fun, the Mysterious and darkly dressed person who in fact is just a teenager in their "all black phase"
• For a mini scenario in the tavern, add a ghost
• The local noble, who pretend to be more important than they are, but you need to deal with them to do anything in that viallage
• The mage and their apprentice travelling for a strange reason in aotally differnet direction

Grizzly McSnarl, this huge, lumbering guy with a bad case of RBF. He never takes a hand off the big-ass knife on his hip. If the players dig a little deeper, they'll learn he's an anxious kind of guy who worries too much about every little thing, and coasts on his intimidating looks to deter trouble.

I just had this happen, sort of, in a completely unplanned way. The party had already met but in the course of events they asked a caravan master to recommend a tavern or inn. He thought for awhile, looked them all up and down, then said “I reckon folks like you would hang out a

<insert inn name>

The party’s face asked what he meant by “folks like you” and he basically said adventurous and prosperous folks.

They went to the inn and the staff and clientele (randomly generated by donjon.bin.sh) were all female, which made them think something was up. The definitely-not-a-face orc ranger tried to befriend the innkeeper and ended up accidentally scaring the crap out of her. I decided it wasn’t that he was personally frightening but that she had mistaken the party for a different, much more nefarious, band.

Based on her bowing and fawning over the party, the other folks in the inn began to stare. At that point, Mr Face decided he needed to talk to every woman in the room.

Ultimately, based on a weird sequence of crit fails and successes, they ended up with a side quest to kill a demon that been terrorizing a nearby village, assisted by two fairly stupid local mercenaries.

I hadn’t planned it but they didn’t know that until I told them to give me 5 minutes to make a new encounter map!

The cast of "piano man" by Billy Joel and don't tell your players

Hollister Nimbleprick, a large nosed halfling tailor/thief, looking to join an adventuring group. He's actually a dwarven fighter in disguise. One the run for the last month, he shaved his beard, took off his boots and swapped his axe for a rapier. If he joins the group, he will complain under his breath anytime they ask him to do thief stuff. He falls every time he tries to climb walls or trips when he tries to sneak around and accidentally triggers every trap he's tasked with detecting.