16th level Expert (Drunkard), 2nd level Philanderer (10th level once beer-goggles are on), 1st level Rogue (Opportunist)
Old as dirt
ET - Ever-thirsty
Bar (30%), Pub (30%), Tavern (30%), Temple of Baccus (10%)
About Whiskey Jack
Whiskey Jack is an aging NPC who hangs out in every fantasy tavern in every RPG known to man. His Knowledge (Bar Lore) +21 is impressive, but he is mostly worthless except for his ability to swindle PCs for fake information in return for bought drinks. Whiskey Jack is an homage to every "old farmer", "aging bar patron", or "ancient guard" forced to hang out in D&D taverns, eternally drunk, who only exists to provide PCs tid-bits of information.
Whiskey Jack's Bar Joke Table (1d6):
1. An elf, a dwarf and a halfling walk into a bar, take a seat and each orders a pint of the freshest ale on tap. While all three are enjoying their newly-poured drafts, simultaneously three flys land in all three of their drinks. The elf pushes his drink away, disdainful, refusing to drink any more of it. The halfling shrugs, carefully picks the fly from his mug, and continues to drink. The dwarf grumbles, pulls the fly from his ale and violently shakes the fly shouting "Spit it out, you wee bastard!!!"
2. One day in the Underdark, a myconoid walks into a bar. The drow bartender says to the mushroom man, "Hey, we don't serve your kind here!" The myconoid hotly responds, "Why not? I'm a fun guy!"
3. A barkeep is surprised to see an skeletal pirate, dripping with sea-weed and barnacles, trudge into his bar. As the undead pirate approaches the bar, and the other tavern patrons flee, the barkeep cannot help but notice a ship's wheel firmly attached to the groin of the pirate. The pirate shuffles to the bar, an unholy croaking voice saying "YAAAR, I be parched to the bone... I'll have a double of ye finest spiced rum." The barkeep, being a high-level barkeep, is non-plussed and pours out the requested drink... but he parlays with the skeleton, "Sir, I can't help but notice that you have a ship's wheel attached to your, um, groinal area." The pirate nods his boney skull, "Aye, I know of it- yar, it be driving me nuts!"
4. A newly ordained Priest of Abadar is nervous about taking confessions and asks an older priest to observe one of his sessions and give him some tips. Afterwards the older priest suggests to him, "Try crossing your arms across your chest, rub your chin thoughtfully with one hand. Then try saying 'I see', 'I understand' and 'Yes, go on'." The younger priest practices this for a while. "Well done," says the older priest, "I think this will work better than slapping your knee and saying 'No way! What happened next?!'".
5. A group of orcs with spears are chasing after three young, buxom hobbit lasses. The three, a blonde, a brunette and a red head quickly take refuge in a farmer's barn. They have time to hide by concealing themselves in burlap sacks. When the band of orcs arrive, they take in the scene before them. "I bet they are in the sacks," the leader orc grunts. One of his warriors took up his spear and was ready to stab the sack with the brunette in it when she called out "mew mew, meow". The warrior stops himself from stabbing the sack, "Nah, this one has kittens in it." He steps over to the next sack containing the red headed hobbit and before he can stab into the sack she calls out "bark, ruff ruff". "Ah, this one has puppies innit." Moving on to the third sack, before the warrior can stick it with his spear, a shaky voice called out "potato? potato?".
6. A wizard is out for a stroll with her lizard familiar when a passer-by remarks "Why, that's a funny-looking reptile you have! What's his name?" The wizard curtly replies "Tiny." The stranger looks confused, then asks "Why?" "Well," the wizard replies "because he's my newt."
Yo mamma jokes for monsters... (pick one at random)
Yo mamma's CR so low her touch AC is "yes".
Yo mamma's CR so low PCs is docked XP for killin' her.
Yo mamma's CR so low she don't have hit dice, just a coin toss.
Yo mamma's CR so low the only sub-type she qualifies for is "mount".
Yo mamma's CR so low she uses a d6 for saving throws.
Yo mamma's CR so low she just has a single stat line.
Yo mamma's CR so low dopplegangers die from cloning her.
Yo mamma's CR so low she can't even do non-lethal damage.
Yo mamma's CR so low if she was a swarm "Alchemist's Fart" would kill her.
Yo mamma's CR so low you'd think she the "LAME" template applied.
Yo mamma's CR so low only a Paladin with "Detect Suck" could find her.
Why "Whiskey Jack" as your username?
I used to run a lot when I was younger- 2-3 miles a day until I injured my foot, after that I stopped running for a while. When I would run, I almost always ran to military cadence. One of my favorite ones went something like this...
Hey, hey, Whiskey Jack
Meet me down by the railroad tracks
Put that C4 in my hand
I'm gonna be a blastin' man
A blastin' man
The best I can
This would cycle through different weapons but I always enjoyed that opening "Hey, hey, Whiskey Jack" line.