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Quite do-able, obviously!
Alessandro Juliani ...was in
Watchmen with Jackie Earle Haley
Jackie Earle Haley was in
The Day of the Locust with Donald Sutherland
Donald Sutherland was in
The Great Train Robbery (1978) with Sean Connery
Sean Connery was in
Murder on the Orient Express (1974) with Ingrid Bergman
Ingrid Bergman was in
Europa '51 with...
Giulietta Masina.
I wasn't sure about that one, because Alessandro Juliani is primarily known for TV and voiceover work, not feature films, but I found something!
(He was the Rockefeller Military Base Technician in
Watchmen.)
Anyway, here's my next one...
Romolo Valli and
Jamie Campbell Bower
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"Well, it's what people know about themselves inside that makes 'em afraid" - Clint Eastwood as The Stranger, High Plains Drifter (1973)
"I'll let you be in my dream if I can be in yours" - Bob Dylan, Talkin' World War III Blues (1963)