Lol normally I always have a different "separation" than you do but it always leads to the same people, but the Paula Abdul one was the same exact one that I thought of too!
answer:
Johnny Depp was in Blow with Penelope Cruz
Penelope Cruz was in Vanilla Sky with Tom Cruise
Tom Cruise was in Jerry Maguire with Kelly Preston
Kelly Preston is married to John Travolta
John Travolta was in Bolt with Miley Cyrus
here ya go:
Kate Winslet and Courtney Love |