RE: DooWop tailgating
To me, tailgating is as much about atmosphere and comradery than anything else. I've been involved in some fairly elaborate tailgates, but have also had a great time simply munching on a sub (hero, hoagie, grinder, bomber, etc.)
That said, if you just buy a cheap little grill and bring a variety of meats and sides (salads, etc.), I bet you'll have a great time.
On another note, I'm 41 but love Doo Wop music, making me one of the few people I know of in my age group who likes it. I'm a sucker for those PBS Doo Wop specials.