h2g2 The Hitchhiker's Guide to the Galaxy: Earth Edition

Beenaway on vacation. Let me get my brain turned back on. This may take awhile...

Got it!

Jack Nicholson was in Easy Rider with Dennis Hopper.
Dennis Hopper was in Waterworld with Kevin Costner.
Kevin Costner was in The Untouchables with Sean Connery.
Sean Connery was in Thunderball with Desmond Llewellyn (and a few others, of course).
Desmond Llewellyn was also in the recent Bond films in which M was played by Judi Dench.

Ok - what about Omar Sharif and Macaulay Culkin?! Surely impossible!

Omar Sharif was in the 13th Warrior with Antonio Banderas
Antonio Banderas was in Philadelphia with Tom Hanks
Tom Hanks was in Splash with John Candy
John Candy was in Uncle Buck with Macaulay Culkin

Whew!

What about Ted Danson and Liza Minelli

Ted Danson was in A Fine Mess with Richard Mulligan
Richard Mulligan was in Micki & Maude with Dudley Moore
Dudley Moore was in Arthur with Liza.

Judi Dench has a Jack Nicholson number of 2.

Judi Dench was in Wetherby (1985) with Vanessa Redgrave
Vanessa Redgrave was in The Pledge (2001) with Jack Nicholson

Jack Nicholson was at the same award ceremony as Judi Dench. There. They also both won prizes. Can I join in? This conversation ended 5 years ago. Hi guys!

How about Leonardo di Caprio and Kate Winslet? Considering you need to do it in exactly five...

And if that's too easy why not try doing it a roundabout way with ten, i.e:

1. Caprio
2. ???
3. ???
4. ???
5. Kevin Bacon
6. ???
7. ???
8. ???
9. ???
10. Kate Winslet
11.???
12.???
13.???
14.???
15. Caprio