
When Willie Nelson cut off his long silver braids in May 2010 at the age of 77, it made headlines across the country, yet the most meaningful haircut of his life had happened twenty-seven years earlier for Waylon Jennings.
In 1983, Johnny Cash and June Carter Cash opened their home to host a celebration for Jennings, who had just fought his way to sobriety after years of heavy substance abuse. Willie was out on the road and could not make the gathering in person, so he cut off his red braids and sent them along with his then-wife, Connie Nelson, to place directly into Waylon’s hands.
Jessi Colter, Waylon’s wife, later recalled that the unexpected gift delighted her husband. Between two men who rarely needed big speeches to understand one another, handing over the most recognizable piece of Willie’s public image was a personal salute to a friend who had just reclaimed his life.
That bond had started almost two decades earlier in Phoenix, Arizona. In the mid-1960s, Waylon was playing regular sets at a local nightspot called JD’s while Willie was still a struggling Nashville songwriter wearing short hair and tailored suits.
When both men grew frustrated with the strict studio rules on Music Row, they went looking for their own creative footing. Willie moved back to Texas in the early 1970s, let his hair grow down past his shoulders, tied on a bandana, and began drawing mixed crowds of traditional country listeners and younger college students.
Waylon fought for the right to use his own touring band in the recording studio, and before long, their separate rebellions merged into a shared movement. In January 1976, RCA Records released Wanted! The Outlaws, a compilation featuring Waylon, Willie, Colter, and Tompall Glaser that became the first country album in history to earn platinum certification for selling a million copies.
Two years later, their 1978 studio album Waylon & Willie gave them a four-week number-one country smash with “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” Through all the sold-out arenas and gold records, however, the pace of the road was taking a severe physical toll on Jennings.
By the early 1980s, a relentless dependency on cocaine and amphetamines was threatening both his career and his health. When Waylon finally walked away from the habit in 1983, Johnny Cash—who knew better than anyone how hard it was to survive addiction in the spotlight—wanted to make sure his friend’s recovery was honored by the people who loved him most.
Getting sober gave Waylon nearly two more decades of music and family life. Only two years after that 1983 party, he and Willie teamed up with Cash and Kris Kristofferson to form The Highwaymen, recording three albums and touring the world together into the mid-1990s.
Waylon and Jessi kept Willie’s 1983 braids stored safely at their home in Arizona through the rest of Waylon’s life. Even after Jennings passed away from diabetes complications in February 2002 at age 64, the pair of red plaits remained among his prized personal keepsakes.
When Willie decided to trim his hair again at his Maui home in May 2010—a change first revealed when television host Jimmy Fallon posted a snapshot of the clean-cut singer online—the motive was much simpler. His publicist, Elaine Schock, confirmed that the 77-year-old troubadour just wanted an easier way to stay cool in the Hawaiian heat before heading back out on tour with his battered guitar Trigger.
Four years after that Maui haircut, on October 5, 2014, Guernsey’s held a public auction of items from Waylon’s estate at the Musical Instrument Museum in Phoenix. Among the instruments and stage wear, the pair of braids Connie Nelson had carried to Johnny Cash’s house thirty-one years earlier drew intense bidding and sold for $37,000.
Willie eventually let his silver hair grow long again as he continued touring into his nineties, while the older red braids went to a private collector. Long before they were worth a small fortune at auction, they were simply one friend’s way of telling another he was glad he was still alive.