Gary Cooper?
You obviously don't know the rules.
You can only include a featured actor/actress that has appeared in a major motion picture in the last 25 years. But I'll play along...
Gary Cooper was in "High Noon" with Lloyd Bridges.
Lloyd Bridges was in "Blown Away" with Jeff Bridges.
Jeff Bridges was in "White Squall" with Scott Wolf.
Scott Wolf was in "Go" with Jay Mohr.
Jay Mohr was in "Jerry Maguire" with Tom Cruise.
Tom Cruise was in "A Few Good Men" with Kevin Bacon.