His friends growing up might have been mentally handicap and didn't realize the bullshit they were listening to. This explains why he thinks he is the best thing ever, and how he thinks he is getting away wit it.
It is best to avoid the 1upper at all costs. If contact is unavoidable, make up stories that no one (less the 1upper) would believe and watch the bullshit flow.
"My roommate takes the shortcut home, but Justin informed us that its not as fast when you drive an extended cab pickup 35mph through the roundabouts on the normal drive. That 1upping peace of shit... he couldn't take those roundabouts at 25mph, but he takes them at 35mph every day...Right"