Six Degrees of Samuel Jackson?

[Mr. DS]

Bruce Li in Yellowthread Street with Bruce Payne
Bruce Payne in Dungeons And Dragons with Jeremy Irons
Jeremy Irons in The Pink Panther 2 with Steve Martin
Steve Martin in Bringing Down The House with Eugene Levy
Eugene Levy in Astro Boy with Samuel Jackson (voice)

Timothy Balme (Lionel from Dead Alive)

[sideorderofninjas]

Timothy Balme to his zombified mum, Elizabeth Moody, in Dead Alive
Elizabeth Moody to Kate Winslet in Heavenly Creatures
Kate Winselt to Kevin Spacey in Life of David Gale
Kevin Spacey to Sam L. Jackson in Negotiator

Rowdy Roddy Piper

[Flick James]

Roddy Piper to Keith David in They Live
Keith David to Chris Tucker in Dead Presidents
Chris Tucket to Sammy L in Jackie Brown

Okay, I'm gonna get serious and go silent era.

Mary Pickford.

[Mr. DS]

Pickford with Leslie Howard in Secrets
Leslie Howard in Gone With The Wind with Vivien Leigh
Vivien Leigh in Ship Of Fools with Lee Marvin
Lee Marvin in Gorky Park with William Hurt
William Hurt in The Incredible Hulk with Tim Roth
Tim Roth in Pulp Fiction with SLJ

Werner Krauss

[sideorderofninjas]

Werner Krauss with Conrad Veidt in Cabinet of Dr. Caligari.
Conrad Veidt with Humphrey Bogart in Casablanca.

Humphrey Bogart with James Cagney in the Roaring Twenties.
James Cagney With Samuel Jackson in Ragtime (1981).

Free reign, let somebody else pick...