Raising the front tire of a motorcycle off the ground, squids use this to determine the alpha male of a group of gixxer riders. The longer the whoolie is held the danker it is.
Dude did you see Greg's dank whoolie? He held it for like two seconds! Fucking sick!
Pajama casual is a term used when working from home and preparing for a video conference. All business above the waist and your pajama pants down below.