Generational Styles Clash

Question Scott, 

What are some weird generational style clashes that just didn't mesh together. Example some of mine were RVD/Mr. Perfect or L.O.D./New Age Outlaws. Basically styles from different eras going at it.

LOD vs RVD & Kane was exceedingly bizarre.  Perfect was like he was from another universe in 2002.  It happened a lot after the Attitude Era because the business changed SO much from the 80s until then, in  such a short amount of time.  All these guys got left behind in dramatic fashion.