Name that show! - Name the really obscure tv show.

[IkeaBoy]

2nd show- Charles Russell dies, but since he is too good for hell and too bad for heaven, he is given the opportunity to go back to 1987 to assist his younger self, Chazz, in making better decisions at critical junctures in his life in order to (hopefully) get into heaven. Has a best friend Booch, 2 nd version of the show (with new name) was much better.

This sounds like a show called Teen Angel that was on ABC for a couple of weeks a couple of years ago. It probably isn't it but you said "second version" of the show existed too so it's worth a shot.

If I'd be allowed to use IMDB I can probably solve all these.