Jessie May Cochran Orr was the fifth child of Henry Owen Cochran and Sarah Frances Reynolds. She was born on 21 February 1884, outside of Mount Vernon proper in a area called Union, which is near Union Presbyterian Church. Jettie attended part of elementary school near Phelps, MO. She married James Paul Orr on 16 March 1905. He originally called on her sister Ida, but when Ida was not ready on time, her mother sent sister Jessie to entertain Mr. Orr. He switched sisters and married Jettie, as she was called.

Jettie's final pregnancy was a difficult one; she had uremic poisoning and fully expected to die. She made each of her children a new outfit so they would have good clothes to wear to her funeral. The baby (Florence) came early and weighed only 3.5 pounds. The doctor wasn't present for the birth, and her older daughters assisted. She had them put towels in the oven to warm them so she could wrap Florence in them to keep her warm. For a time, she stayed with her sister Estelle, and they sat Florence in a shoebox on the oven door to keep her warm.

Jim Orr died in 1922, leaving her nine children to raise. She worked in a sanitorium to support herself and children, some of whom had to live in the Odd Fellows Home in Liberty, MO because she could not fully support them financially. There were no welfare payments for widowed women in the 1920s.

When the children first went to Liberty, the baby, Florence, went with them, and sister Lib cared for her. After a month, the home wrote to Jettie and said they could not keep a child that young. Jettie traveled to Liberty and stayed there for several months. She kept Florence with her and worked as a housekeeper for a local doctor. A couple of times a month she would pay for a cab and she and Florence would go visit the other children on a Sunday. Eventually, she moved back to Mount Vernon, where her support system was and she could get a better job. Her sister Estelle (Aunt Stell) was postmistress in Bowers Mill (near Carthage), and she took Florence to work with her.

Over time the children returned from Liberty and lived in the very tiny house that Jettie had bought in 1927 with the small insurance policy she received when her husband died. There was a large newspaper article about how she was a huge fan of Mount Vernon High School football, since three of her sons (Harold, Miles, and Tommy) all played in 1933. Times were not all fun. Daughter Elizabeth reports that she once had to take out a second mortgage on the little house because her grocery bill had grown so high and the grocer demanded payment. Jettie lived in that little house for 35 years.

During World War II, Jettie decided that if she was going to get to see her three sons who were in the service that she should move to Washington, D.C., where her daughter Marguerite Orr Harlowe and husband Clarence lived. Jettie lived with them for a time, then rented a large home from a woman whose husband was stationed elsewhere in the U.S. Jettie opened a rooming house. She returned to Mount Vernon after the war. She broke her hip in the 1950s, and eventually was in a wheelchair. She believed that if you sewed a stich on Sunday, you would have to rip it out with your nose before you could enter heaven. Jettie died at the home of her daughter Mary Frances (Tancy) Orr Schnake, in Stotts City, MO in July 1963.