i figured out several possibilities:

Kevin Bacon & Jennifer Aniston (Picutre Perfect....or whatever the fuck it's called)

Jennifer Aniston & Brad Pitt (and episode of "Friends")

Brad Pitt & Angelina Jolie (Mr. and Mrs. Smith)

Angelina Jolie & James Duval (Gone In Sixty Seconds)

James Duval to Gragg Araki

OR: Angelina Jolie & Angela Bettis (Girl Interupted)

Angela Bettis & James Duval (May)



you could also link Kevin Bacon & Brad Pitt together from the movie Sleepers, following the same route stemmed from Brad Pitt


OR:

Kevin Bacon & Tim Robbins (Mystic River)

Tim Robbins & Amanda Bearse (Amanda Bearse, as you know, played Marcy on the show "Married With Children) in the movie Fraternity Vacation (old cheesy 80's movie)

and Amanda Bearse had a cameo in Doom Generation

***also, interesting to note, you have Stephen Geoffery's (who was a crappy actor in the 80's, who later became a gay porn star, from my home-city of Cincinnati, Ohio...w00t! w00t!) who was in Fraternity Vacation as well as the movie Fright Night (also with Amanda Bearse), but the real key actor here is Chris Sarandon (who was the voice of Jack Skeleton in Tim Burton's The Nightmare Before Christmas) but he was also in the movie The Princess Bride (playing Prince Humperdinck) which had Robin Wright-Penn (Sean Penn's wife, Sean Peen having been in Mystic River), but Christopher Guest is also in The Princess Bride (playing Count Tyrone Rugen) who is the director and star of Waiting For Guffman, Best In Show and A Mighty Wind all of which star Parker Posey, who also had a cameo in Doom Generation....also, Matt Keeslar (from Splendor) is in Waiting For Guffman


OR:

Kevin Bacon & Neve Campbell (Wild Things)

Neve Campbell & Rose McGowan (Sream)

Rose McGowan obviously in Doom Generation

OR:

Neve Campbell & Parker Posey (Scream 3)

Parker Posey's cameo in Doom Generation



so yeah, there's multiple ways....prolly a shit ton more......and i know, i'm a geek, but my friends and i used to play SIX DEGREES a lot, just not with Kevin Bacon either....

another good actor to use is Bill Paxton (Titanic, Aliens, Frailty)......i'll see if i can't find a way to throw him in the mix some way....