Karen Black was in The Player with Tim Robbins
Tim Robbins was in Mystic River with the Kevonator

Carmen Electra

Carmen Electra was in Scary Movie with Shannon Elizabeth, who was in Thirteen Ghosts with Matthew Lillard, who was in Scream with Neve Campbell, who was in Wild Things with Kev Theft Auto

Johnathon Jackson was in Tuck Everlasting with Elizabeth Shue
Elizabeth Shue was in Hollow Man with Kevstopher

still Carmen Electra

Iggy Pop

Iggy was in Coffee and Cigarrettes with Steve Buscemi
Steve-o was in 28 Days with Viggo Mortensen
Viggo was in Psycho remake with Vince Vaugh
Vince was in Anchorman with Tim Robbins
Tim Robbins was in Mystic River with the Kevster

Samuel L. Jackson

Sameul Jackson was on Die Hard:With a Vengeance with Bruce Willis, who was in The whole nine yards with Amanda Peet, who was in Saving Silvermen with Jason Biggs, who was in American Pie with Mena Suvari, who was in American Beauty with Kevin Spacey, who was in Pay it Forward with Helen Hunt, who was in As Good as it Gets with Jack Nicholson, who was in a Few Good Men with Bacon on Rye

Peter Boyle

samuel l jackson is in a time to kill with kevin spacy who's in seven with brad pitt who's in sleepers with kevin bacon ;)

I win!