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He married Leslie Corkhill Redlich in San Francisco in 1977 and together they have three children, Chloe Frances Cockburn (April 3, 1979), The O.C. and House M.D. actress Olivia Wilde (née Olivia Jane Cockburn) and Charles Philip Cockburn (January 31, 1993).
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He then began covering middle eastern subjects, including the 1991 documentary on the after-effects of the first Gulf war, The War We Left Behind, which he co-produced for PBS with Leslie Cockburn.
Journalists Laura Flanders and Stephanie Flanders are his half-nieces, daughters of his half-brother in law Michael Flanders, and actress Olivia Wilde, is his niece, daughter of his sister in law Leslie Cockburn.
He has also produced numerous documentary films, principally in partnership with Leslie Cockburn as well as co-producing the 1997 thriller The Peacemaker, starring George Clooney and Nicole Kidman, for Dreamworks.