Most accounts of Cooper's life focus on three facets of his 39 years: his emotional reporting on Hurricane Katrina, his famous mother, and his brother's sudden, unexplained suicide. In the summer of 1988 Cooper's older brother Carter took his own life by dangling from the terrace of the family's 14th-story penthouse, then letting go – with his mother right there, begging him not to do it. His last words were, "Will I ever feel again?"
In retelling Anderson's story, his brother's suicide is often cited as the seminal event that triggered him to begin traveling the world, reporting on tragedy. In his memoir he writes of "wanting to go where the pain outside matched the pain I was feeling inside." While this connection has certainly played large in Cooper's psyche, it's not the complete picture. He actually began traveling, and seeking his own identity through tests of character, during high school. At that time in his life his brother was at Princeton. His father, Wyatt Cooper, had died undergoing open heart surgery when Anderson was 10. His mother was nearing the peak of her success with designer apparel and was seeing the same astrologist as Nancy Reagan. Young Anderson sought his own alternate universe too.
He found it the summer before his junior year, in 1983, when he spent time in the Rockies with NOLS, the National Outdoor Leadership School. Having grown up on the Upper East Side of Manhattan as the son of a fashion maven, Cooper had never carried a backpack, let alone done any proper mountaineering. Within minutes of stepping off the plane in Cheyenne, Wyoming, the guides voted him least likely to survive the course. After a month in the Wind River Range, Cooper had found the antidote to the chaotic silliness of Manhattan high society and the infamous romances of his mother. This contrast – between his mother's life and the one he wanted for himself – is a recurring theme in his life.
Cooper had hoped to spend his senior year of high school at Scotland's notoriously rugged Gordonstoun School, which was started by Dr. Kurt Hahn, the same man who founded Outward Bound. When that didn't work out, he completed his high school credits in one semester. Most 17-year-olds would have seen the forthcoming months as a chance to drink beer by the gallon while waiting to hear if they'd been accepted to college (Cooper later was, to Yale). Instead Cooper fixated on an ad in the back of an adventure magazine for a company called Encounter Overland that promised a trip through Africa in a 13-ton British Army truck. Cooper bought a seat on the truck and flew to Johannesburg.
In the back of the truck he was surrounded by dropouts from Australia, guys in their 20s and 30s who didn't know what to do with their lives. For months the group made camp and cooked their own food. Wherever they camped, locals would come out and sit, watching. Cooper would play with the kids, kick a soccer ball around with the teens, and do his wash with the villagers. "Africa was a place to forget and be forgotten in," he later wrote.
One night, as Cooper slept under the truck, the camp was raided and everything was stolen, including Cooper's clothes, camera, and film. He wasn't upset about the clothes, but the loss of the film troubled him. Without pictures from his trip, he feared he'd forget some of what he learned en route. He decided to see the theft as a test, a chance to prove that he wasn't caught up with owning the right things.
Months later, the trip ended in the Central African Republic. Cooper flew home to New York, where he found his mother at their house in Southampton. Friends were over; small talk was being had on the porch. Welcome back to the land of things.