I vaguely remember watching a TV show some 20-odd years ago, but remember only a few details from the pilot episode:
1) This guy dies, and is told he has to go back in time to watch over some teenager 2) In an attempt to make life easy for the teen and his family, he gives the teen a lottery ticket that he thinks will win millions of dollars. Instead, he missed a couple of numbers, and the teen won a much smaller amount 3) The guy is then invited to stay with the teen, and the guy looks up to heaven with a bit of a concerned look about how long he'll have to stay on earth before he can go to heaven.
If I remember correctly, the show also only lasted about 1 season.