This may be fun or it may be boring. Kind of a six degrees of seperation thing.
Example (and an extreme one) Beatles to Johny Depp. And once more god bless Wiki.
1. Beatles performed with Billy Preston.
2. who played with Red Hot Chilli Peppers
3. who used Rain Phoenix as a touring backing singer
4. who was the sister of River Phoenix
5. who was a friend of, and died in the nightclub owned by...Johny Depp.
I can do The Beatles to Harvey Keital in 4. (all from Wiki, working backwards of course.)