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From the late 1960s until his retirement, Cobb focused on his petroleum and timber interests. In 1938, Cobb married the oil heiress Audrey Umsted, whom he had met while golfing. Her father, Sydney Albert Umsted, had in 1924 drilled the Discovery oil well in the Smackover field but was subsequently mortally injured in a train accident in [[Mississippi]] and died in a hospital in [[Memphis]], Tennessee.<ref>Cobb, pp. 77-78</ref> The Cobbs adopted one son, John Cobb. Audrey Cobb died in 1976. The next year he married his neighbor, Martha Jane Rebsamen,<ref name=bio/> the widow of Raymond Rebsamen, a prominent Little Rock industrialist and philanthropist.<ref>Cobb, p. 157</ref> Shortly before the second marriage, two armed robbers wearing masks broke into Martha Jane's home and locked her, Cobb, and her housekeeper in a closet. The intruders left with Cobb's Cadillac but called police to tell them of the three people trapped in the closet.<ref>Cobb, p. 159</ref>

From the late 1960s until his retirement, Cobb focused on his petroleum and timber interests. In 1938, Cobb married the oil heiress Audrey Umsted, whom he had met while golfing. Her father, Sydney Albert Umsted, had in 1924 drilled the Discovery oil well in the Smackover field but was subsequently mortally injured in a train accident in [[Mississippi]] and died in a hospital in [[Memphis]], Tennessee.<ref>Cobb, pp. 77-78</ref> The Cobbs adopted one son, John Cobb. Audrey Cobb died in 1976. The next year he married his neighbor, Martha Jane Rebsamen,<ref name=bio/> the widow of Raymond Rebsamen, a prominent Little Rock industrialist and philanthropist.<ref>Cobb, p. 157</ref> Shortly before the second marriage, two armed robbers wearing masks broke into Martha Jane's home and locked her, Cobb, and her housekeeper in a closet. The intruders left with Cobb's Cadillac but called police to tell them of the three people trapped in the closet.<ref>Cobb, p. 159</ref>

In 1989 and 1990, with the help of the late journalist-editor Carol Griffee, then of Little Rock, Cobb published two editions of his autobiography entitled ''Osro Cobb of Arkansas: Memoirs of Historical Significance''. He died in Little Rock at the age of ninety-one. His papers were deposited in Special Collections of the Torreyson Library of the University of Central Arkansas in Conway.<ref name=bio/>

In 1989 and 1990, with the help of the late journalist-editor [[Carol Griffee]], then of Little Rock, Cobb published two editions of his autobiography entitled ''Osro Cobb of Arkansas: Memoirs of Historical Significance''. He died in Little Rock at the age of ninety-one. His papers were deposited in Special Collections of the Torreyson Library of the University of Central Arkansas in Conway.<ref name=bio/>