My first time playing, so let me try:
Rosalind Elliot -
Murders in the Rue Morgue

• Jason Robards -
  Magnolia
• Philip Seymour Hoffman -
  Cold Mountain
• Cillian Murphy
  Next one: Judi Dench

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Norman Reedus was in the Conspirator with Com Meaney
He was in Bitter Harvest (When Harry became a Tree) with Cillian
Next: Robby Benson
John Lennon (1940-1980)
Wherever you are, you are here

Colin McCredie was in Pandemonium wi5b4th Andy Serkis
Who was in "13 Going On 30" with Jennifer Garner
Who was in Valentines Day with Anne Hathaway
Who was in "The Dark Knight Rises" with Cillian Murphy.
Next: Norman Reedus

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Liam Gaffney was in The Avengers (1960's TV Show) with Patrick Macnee who was on
Frasier with Laura Linney who was in
Savages with Phillip Seymore Hoffman who was in
Cold Mountain with Cillian Murphy.
Next: Colin O'Donoghue

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Fran Drescher - Timothy Dalton - The beautician and the beast
Tim Dalton - Jennifer Connelly - Rocketeer
Jennifer - Cillian - Cry/Fly
Next: Paul Newman
John Lennon (1940-1980)
Wherever you are, you are here

Olivia Hussey - Michael York: ROMEO AND JULIET
Michael York - Michael Caine: AUSTIN POWERS IN GOLDMEMBER
Michael Caine - Cillian Murphy: BATMAN BEGINS
Next: Fran Drescher

Christopher Reeve - Jane Seymour - Somewhere in time
Jane Seymour - Rachel McAdams - Wedding Crashers
Rachel - Cillian - Red Eye
Next: Olivia Hussey
John Lennon (1940-1980)
Wherever you are, you are here

Fred Savage - Michael Caine: AUSTIN POWERS IN GOLDMEMBER
Michael Caine - Cillian Murphy: BATMAN BEGINS
Next: Christopher Reeve

Aisha Tyler was in Balls of Fury with Chr111cistopher Walken
Christopher Walken was in Wedding Crashers with Rachel McAdams
Rachel was in Red Eye with Cillian
next: Fred Savage
John Lennon (1940-1980)
Wherever you are, you are here

Yep, you're right. I got my "In's" mixed up.
~ j'adore faire l'amour ~

Actually sweetie Colin and Cillian were togetheer in 'Intermission' not Inception
John Lennon (1940-1980)
Wherever you are, you are here

Alright, I'm going to throw out another name to keep the game going.
Aisha Tyler
~ j'adore faire l'amour ~

Michael Fassbb68ender was in Hunger with Liam Cunningham.
Liam was in the Wind that Shakes the Barley with Cillian.
Hopefully they will work together someday.

Geraldine was in The Impossible with
Naomi Watts
.
Naomi was in J. Edgar with
Leonardo Dicaprio
.
Leo was in Inception with Cillian.
Next: Michael Fassbender.
I'm Bane yes, that's my name. When you hear the name Bane, I guarantee the pain. Im coming after you, Bruce Wayne. Im stronger, smarter, clinically insane.
This love will be your downfall

Kevin Costner - Demi Moore: MR. BROOKS
Demi Moore - Robert DeNiro: WE'RE NO ANGELS
Robert DeNiro - Cillian Murphy: RED LIGHTS
Next: Geraldine Chaplin

I think TV shows could be allowed, with the exception of SNL, 'cause that would be too ea111csy
Matthew was in Wicker Park with Rose Byrne
Rose was in Sunshine with Cillian
Next: Kevin Costner
John Lennon (1940-1980)
Wherever you are, you are here

I know there would be Glee connections, but I've just never been sure if we're allowed to use TV shows.
Betty was in You Again with Sigourney Weaver
Sigourney was in Red Lights with Cillian
Next: Matthew Lilliard
~ j'adore faire l'amour ~

There are way less degrees between Cillian and Cory (may he rest in peace )
Cory was in Glee with Jayma Mays
Jayma was in Red Eye with Cillian
As for Malcom McDowell
Malcom was in I'll sleep when I'm dead with Clive Owen
Clive was in Children of Men with Michael Caine
Michael was in Christopher Nolan's Batman and Inception with Cillian
Next: Betty White
John Lennon (1940-1980)
Wherever you are, you are here

Okay, without using TV shows (because I never know if that's allowed or not)
Cory was in Monte Carlo with Andie MacDowell
Andie was in Four Weddings and a Funeral with Kristin Scott Thomas
Kristin was in The English Patient with Ralph Fiennes
Ralph was in In Bruges with Brendan Gleeson
Brendan was in Breakfast on Pluto with Cillian
Next: Malcolm McDowell
~ j'adore faire l'amour ~

james gandolfini was in violet and daisy with saoirse ronan
saoirse was in atonement with keira knightley
keira was in the edge of love with cillian
next: we'll do this one in memory of Cory Monteith. R.I.P.

Vivien was in a Street car named desire with Marlon Brando
Brando was in Don Juan de Marco with Johnny Depp
Johnny is in Trascendence with Cillian
Next: James Gandolfini
John Lennon (1940-1980)
Wherever you are, you are here