I'll start with Sarah Michelle Gellar.
Sarah Michelle Gellar was in She's All That with Gabrielle Union.
Gabrielle Union was in The Box with Giancarlo Esposito.
Next: Robert De Niro
Currently Watching: Blind Horizon
Giancarlo Esposito was in Last Holiday (2006) with Timothy Hutton
Timothy Hutton was in Good Shepherd, The (2006) with Robert De Niro
Next is Troy Donahue.
shareTroy Donahue was in Godfather Part II with Robert DeNiro who was in We're No Angels with Sean Penn who was in TAPS with Giancarlo Esposito
Next Michael Rooker
Michael Rooker>Cliffhanger>Bruce McGill>Ali>Giancarlo
James Roday?
Who tha heck is James Roday?
There are no problems that cannot be solved with a can of brake clean and a lighter
I didn't check whether tv shows count buttt
James Roday ->Psych->Ray Wise->Bob Roberts->Giancarlo Esposito
Rosie O'Donnell
O'Donnell as in The Flintstones with John Goodman
Goodman was in The Big Lebowski with John Turturro
Turturro was in Do The Right Thing with Giancarlo.
next: Terry Serpico (very easy)
Nothing is as it seems so I wouldn't judge by what you think you see.
Terry Serpico starred with Armin Mueller-Stahl in THE PEACEMAKER
Armin Mueller-Stahl starred with Giancarlo Esposito in NIGHT ON EARTH
Next is Roland Gift (as an actor)