The path towards finding one’s true love may be easy to some, while for others, it is a long, winding, and exhausting road. This is why the story of country singer and songwriter, Willie Nelson, of finding his one true love has become quite an infamous one. 

After his long history of failed marriages and relationships ending on a bitter note, it seems that his fourth and current wife, Annie D’Angelo, is here to stay. D’Angelo has been Nelson’s wife for almost three decades, and she has proven to be his rock through life’s ups and downs.

How did the “Always on My Mind” singer finally found his great love? Let’s do some digging into one of the greatest love stories in country music.

There Were First Several Painful Chapters 

American singer and songwriter, Willie Nelson, is one of the world’s most accomplished musicians. He has been known for his Outlaw Country songs with hit singles like “Crazy” and “On the Road Again.”

In 1952, Nelson married his first wife, Martha Mathews, a marriage that would only last for ten years. His marriage with Mathews became a contentious and violent one. The last night of their marriage was the most garish one. In Nelson’s 1980 interview with People, the country legend recalled the one night he came home drunk. While Nelson was passed out, Mathews sewed him up in a sheet and started beating him with a broomstick.

“I woke up in this straitjacket, getting pounded like a short-order steak,” Nelson told People. By the time he got loose, Mathews had lit out in the car with their kids, her clothes, and even the ones owned by Nelson. Of course, there’s no way Nelson could follow her naked, so “that was kind of the end of it.” Nelson and Mathews had three kids together: Lana, Susie, and Willie “Billy” Hugh, Jr.

A year after Nelson and Mathews went separate ways, the country legend married fellow country singer Shirley Collie. They were husband and wife singing, recording, and traveling together. They settled down on 200 acres near Nashville in 1964.

However, this marriage ended almost as bizarrely as Nelson’s first. Things had quickly gotten sour when Collie discovered a bill from a maternity ward in one of the hospitals in Houston. It was charged to Nelson and Connie Koepke for the birth of their child Paula Carlene. Nelson and Collie drifted into smashing up cars, drinking, drugs, and infidelity until the marriage simply died of neglect. 

Even before the divorce from Collie was final, he had gone ahead and married Koepke. By 1970, Collie had moved out, and Koepke had moved in. They eventually had another child, Amy Lee. But this one wasn’t meant to last either. Nelson and Koepke divorced in 1988.

The “On the Road Again” singer finally decided to take a few years off from being married to someone. He didn’t marry again until 1991 when he tied the knot with his current and fourth wife, Annie D’Angelo.

Finding Love The Fourth Time

Annie D’Angelo was living a private and simple life before she met and shared her life journey with Willie Nelson. She was a professional makeup artist, but little did she know that’s how she will meet the country legend. 

In the 1980s, D’Angelo worked in the makeup department for several movies, and this includes the 1986 western drama film Stagecoach, which starred Nelson as Doc Holiday. After their very first encounter, they started sharing a good bond as great friends, but their relationship naturally developed into a romantic one.

Later on, they started dating one another, and without delay, the happy couple, Willie Nelson and Annie D’Angelo tied the knot on September 16, 1991, in Nashville at the St. Alouin Church. Nelson was still married to Connie Koepke when he first met D’Angelo; hence the singer described her as the “great love affair in my life.”

For Nelson, finding love again after three failed relationships helped him to steer his fourth marriage to a relatively more successful path. The couple was blessed with their first child, Lukas Autry Nelson, when he came into the world on December 25, 1988. The couple was again blessed with their second child, Jacob Micah Nelson, when he was born on May 24, 1990.

Nelson has admitted that his marriage with Annie D’Angelo is, by no means, perfect. Just like any couple, they also went through some ups and downs. “I’m not easy to live with. I’m pretty temperamental, you know. “Nelson told Parade, especially that he has been used to doing things on his own for quite some time and he’s not interested in any suggestions.

Nelson also recalled how there has always been friction with his previous wives. But D’Angelo and Nelson got along together. “It takes a special person to live with me,” Nelson said. 

To Nelson, his marriage works because, “well, I now understand a lot more than I did.”

Nelson later admitted, “It’s love that brought Annie and me together, and it’s love that, nearly thirty years later, has kept us together. When it comes to romantic relationships, that’s a record for me.” Indeed, it took the country singer “a damn near a lifetime to get it right.” 

Through Thick and Thin For Three Decades

Nelson has indeed gone through so many heartbreaks, it’s great how he was able to keep his sense of humor and at the same time remain hopeful about his marriage to Annie D’Angelo. When he was asked in a 2012 interview if he thinks that D’Angelo was “the real love of his life.”  

Nelson jokingly responded by saying, “Well, for the moment she is.” Nelson later told Rolling Stone how he found stability in D’Angelo. “She’s been with me through thick and thin.”

She has been with him through the worse parts. Just a few months after they got married, Willie’s first son, Billy Nelson, was found dead in his log-cabin home in Davidson County, Tennessee. A Medical Examiner confirmed that the death was a suicide.  

Billy was 33-years-old then, and his tragic death left his father shocked and crushed. Nelson later looked back on the moment he heard the devastating news. “I’ve never experienced anything so devastating in my life,” he said. It was indeed one of the darkest moments in Nelson’s entire life; luckily, he has D’Angelo by his side to mourn with him and offer comfort.

Now, everything seems going smoothly with the music icon’s life. Willie Nelson’s spouse has been supportive in everything Nelson would do, even all sorts of activism, social justice, and conservation efforts

For instance, in 2017, Nelson and D’Angelo have been vocally supporting the protests against the Dakota Access Pipeline at Standing Rock. The couple was even very generous that they donated enough money to build a shelter for the Water Protectors. Nelson and D’Angelo are also strong supporters of animal rights, environmental activism, local farms, as well as the Occupy Wall Street movement.

In early 2018, D’Angelo has also become Nelson’s business partner. Nelson announced that they had raised about $12 million to expand his latest business venture, Willie’s Reserve, a line of cannabis products garnered from responsible growers, which he founded in 2015. It aims to deliver Nelson’s herbal remedy of choice to customers located in states which have legalized the product.

And recently, D’Angelo is piggybacking on Nelson’s marijuana advocacy as she announced her own business, Annie’s Edibles. Annie’s Edibles makes its debut with artisan chocolates as the first product and is now available at select dispensaries in Washington State.

Nelsons’ friends also credit D’Angelo for keeping Nelson healthy. The couple bike and swim at their second home in Maui, and she has helped him cut back on bacon. She also helped bring down his payroll. Different sources have said that many people were taking financial advantage of Nelson’s generosity. “There were a lot of people sponging off him, even though he didn’t look at it that way,” says Johnny Bush, Nelson’s close friend.

The couple is now spending most of their days either on their Spicewood, Texas ranch, or at their relaxing home in Maui, Hawaii. And since the country superstar has no plan on retiring or slowing down, the couple also spends time together traveling for different concerts on Nelson’s tour bus.  

As for Willie Nelson’s Children with Annie D’Angelo, both have chosen to follow the footsteps of their father on becoming a musician. Lukas has particularly been able to achieve much better success in the industry.

He is a member of an American country rock band named Promise of the Real, sometimes referred to as POTR. The group has been the backing band for Canadian singer Neil Young ever since 2015. Lukas’ band has recorded two studio albums, a soundtrack album, and a live album with Young. He has also been a big part of the film A Star Is Born. He wrote songs for the movie and even appeared in it.

Micah, on the other hand, has performed at many events such as FarmAid, Coachella, and Neil Young’s Bridge School Benefit. His style is non-traditional and “heavily influenced by movie soundtracks.” He performs as ‘Particle Kid’ and also performs with his band known as Insects Vs. Robots.

annie d'angelo and willie nelson with kids

In October 2017, Lukas, Micah, and Willie Nelson dropped the collaborative album “Willie Nelson and the Boys.” The 12-song-album features mostly of covers of country standards made famous by other top country acts. The track “Healing Hands of Time” is the only Willie Nelson original cut for the record.

Nelson’s path to love is absolutely not a conventional one, but it’s inspiring enough to make us believe that true love exists. We wish him many more years with Annie D’Angelo!