The closest I ever got to a 300 was starting with 8 straight Xs. That's nerve wracking as all hell.
Once saw a guy, and this was bittersweet, hit a 299 (sparing on his 11th ball). It was epic. We were in a league that we so appropriately named ourselves the BS league and he was easily the best bowler. No problem with that it's just that he knew he was and he made sure eveyone knew it.
There were more smiles on people's faces than there were "Oh, I'm sorry, man, good game!"