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Four times.
The Shootist
maureen ohara
John WayneMaureen O'HaraPatrick WayneStefanie Powers
Amongst the listed co-stars are Joanne Dru, John Agar, Ben Johnson, Harry Carey Jr, Victor MacLaglen, and Mildred Natwich.
John Wayne produced, directed, and starred in (and partially funded) the 1960 movie about the Alamo.
John Wayne never co-starred with anyone named Diane... the closest I can find is Diana Muldaur (McQ) and Diana Gibson (Adventure's End)
John Wayne starred in The Green Berets.
john wayne.
John Wayne
John Wayne in "Wake of the Red Witch"
No, they never starred together.