(Richard Pryor - Harlem Nights) Eddie Murphy - Harlem Nights Robert DeNiro - Showtime Brad Pitt - Sleepers (George Clooney - Oceans 11)
Not the way I would've gone, but correct nonetheless. I was thinking: Pryor-The Toy Gleason-Smokey and the Bandit Reynolds-Boogie Nights Wahlberg-Three Kings Clooney
Taking in the nature of these stars, it only seems right using actors with cult followings. Robert Englund in Freddy's Dead:The Final Nightmare with... Yaphet Kotto who was in The Puppet Masters with... Keith David who was in Requiem for a Dream with... Christopher Mcdonald who was in *61 with... Anthony Michael Hall (although he likes to be called Michael Hall).
I had: (Englund - Urban Legends) Jared Leto - American Pyscho (cool crazy movie) Christian Bale - Little Women Winona Ryder - Edward Scissorhands (A.M. Hall - Edward Scissorhands) that one was pretty hard huh?
Let's keep this going! Obviously, I'm out of my league with Sonny, RM95, and DBC, but I will try to keep up nonetheless. Here is one that I don't know is easy or not.... Find the actor/actress that connects Cary Grant with Agnes Moorehead (Endora from Bewitched).
Probably not the answer you had in mind, lol, but it works. Dennis Hopper was in "True Grit" with John Wayne and was also in "Welcome to Hollywood" with Will Smith. Will Smith was in "The Legend of Bagger Vance" with Matt Damon.
Also could have used Leo G Carroll who was in North by Northwest with Grant and The Swan with Moorehead.
(Annette Bening - The Siege) Bruce Willis - Pulp Fiction John Travolta - Face/Off Nick Cassavetes - The Independent (Bob Odenkirk - The Independent) I found so many that were only 2 actors apart and one that was four actors apart, took me a while... Here is the two actor: (Bob Odenkirk - Wayne's World 2) Christopher Walken - Pulp Fiction Bruce Willis - The Siege (Annette Bening - The Siege)
I can do it in fewer: Jason Alexander was in Rocky & Bullwinkle with Robert DeNiro who was in This Boy's Life with Leonardo DiCaprio. Or Jason Alexander was in The Last Supper with Bill Paxton who was in Titanic with Leonardo DiCaprio. And with two actors, I got: Jason Alexander was in Shallow Hal with Gweneth Paltrow who was in The Royal Tennenbaums with Gene Hackman who was in the Quick and the Dead with Leonardo DiCaprio. And with three, I got: Jason Alexander was in Shallow Hal with Gweneth Paltrow who was in The Pallbearer with Barbara Hershey who was in The First Wives Club with Victor Garber who was in Titanic with Leonardo DiCaprio. But that's probably not the one you were thinking of.
Yeah I had: (jason alexander - coneheads) david spade - lost & found martin sheen - the dead zone tom skerritt - poison ivy (leonardo decaprio - poison ivy) where is your trivia mrpaige?
I was thinking Odenkirk-The Cable Guy Jack Black-High Fidelity John Cusack-The Grifters Annette Bening OK, do Jim Carrey to Lee Majors using 3 actors.
(Jim Carrey - Truman Show) Ed Harris - Apollo 13 Kevin Bacon - My Dog Skip Frankie Muntz - Big Fat Liar (Lee Majors - Big Fat Liar)