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Exclusive Insider Scoop: Wild Revelations from Willie Nelson’s 90th Birthday Bash

Not only is Willie Nelson one of Maui’s most recognizable celebrity residents, but he’s also truly an American musical icon. Ever the inspiration, he recently celebrated his 90th birthday in grand fashion, with one of the best two day concerts I’ve ever been to!

There’s no doubt, I will forever remember April 29 and 30, 2023 for the show he put together at the historic Hollywood Bowl. A milestone event. One that brought together music enthusiasts from all walks of life, paying tribute to the enduring talent and legacy of this remarkable artist.

Willie Hand Selected A Lineup: One For The Ages

Willie Nelson’s 90th Birthday Celebration showcased his reach and influence across not only the musical industry, but the entertainment industry as a whole. Those who know me, know that I’m a die-hard live music aficionado. I’ve been to hundreds of concerts. Dozens of festivals. So don’t take it lightly when I say that the lineup over these two days rivaled some of the best I’ve seen in over 50 years. Just take a look at the list of talent below!

Keith Richards, Snoop Dogg, Dave Matthews, George Strait, Beck, Chris Stapleton, Miranda Lambert, Neil Young, The Lumineers, Gary Clark Jr., Sheryl Crow, Jack Johnson, Billy Strings, Bobby Weir, Booker T. Jones, Buddy Cannon, Charley Crockett, Charlie Sexton, Daniel Lanois, Dwight Yoakam, Edie Brickell, Emmylou Harris, Jamey Johnson, Kris Kristofferson, Leon Bridges…

Lily Meola, Lukas Nelson, Lyle Lovett, Margo Price, Nathaniel Rateliff, Norah Jones, Orville Peck, Particle Kid, Rodney Crowell, Rosanne Cash, Shooter Jennings, Stephen Stills, Sturgill Simpson, The Avett Brothers, Tom Jones, Tyler Childers, Warren Haynes, Waylon Payne.

Further highlighting his Hollywood connections, there were special tributes and presentations by Chelsea Handler, Ethan Hawke, Helen Mirren, Jennifer Garner, Owen Wilson and Woody Harrelson. The love was endless for a man many have listened to their entire lives. The aloha spirit was thriving these couple of evenings in the City of Angels.

What Had The Crowd Buzzing?

To select any singular moment that defined the show would be a fool’s errand. There were just that many special songs and tributes performed. Some artists sang right alongside Willie, joining him for duet performances featuring his greatest hits. Others belted classic ballads that Willie helped make famous, or songs where Willie himself was the direct inspiration. Having said that, there were a few acts that had the crowd begging for more.

I have to say, it might just be a tossup for biggest “surprise guest” of the evening. One was definitely Keith Richards of The Rolling Stones. When he walked on stage, the whole venue lit up in excitement.

Another notable surprise was when Neil Young brought out long time friend (and Crosby, Stills, Nash and Young band-mate), Stephen Stills.

Ending the evening was an additional crowd roaring surprise, George Strait. As (in my humble opinion) a living member on the Mt. Rushmore of Country Music, Strait’s surprise arrival might’ve been the climax of the first night. “Hey George, let’s sing one,” Willie said after George Strait appeared to our thunderous applause.

As the applause to their first song died down, Willie teased us, saying there was a song he “always wanted to do.” Then he and Strait unwound the epic tale of wayward hustlers, “Pancho and Lefty.” Strait’s voice golden and strong, with Willie’s notes rising, falling and catching like dusty, dry wind. Reminding us that his is the perfect vehicle for capturing the poetry of the American West.

One more highlight happened just after George finished. It was none other than LA native, Snoop Dogg. The hip-hop mega star showed his cross-genre prowess, helping with an especially entertaining version of Willie’s classic track, “Roll Me Up and Smoke Me When I Die”. There’s a short list of people who can have a soul roaring duet with George Strait and then seamlessly transition into a light hearted sing a long with Snoop Dogg. There’s probably only one where you can say “yeah, that makes sense.”

Willie’s catalog is so vast that even with this many musicians, there were hardly any repeats over the two nights. One song, however, was so popular that it absolutely HAD to be played both evenings!

Why Does Jack Johnson Regret Playing Poker with Willie Nelson?

Some of the night’s best moments happened as the artists shared personal stories about Willie. He really is a modern musical influence, whose impact might just be second to none. He’s famous for saying there’s nothing to “a good song (but) three chords and the truth.” Well, Hawaii born Jack Johnson shared with the crowd a song that epitomizes that saying; a story that I was fortunate enough to experience first-hand, witnessing the events that let to the song’s inception.

On April 19, 2006, Johnson was headlining the ever popular Maui Earth Day Concert, his annual Kokua Festival. After the show, Willie invited a crew to Django Lounge, the legendary poker room at his North Shore Maui home. I was lucky enough to have a seat at the table; literally in between Jack and fellow talented musician, Ben Harper. Check the videos above and below to hear the whole story; but to keep it short, the vibes around the table were especially high.

The drinks were flowing, and a lovely smelling haze encompassed the air. A story as old as time, those around the table tried to keep up with the legend at his game. As the evening unfolded, this dream card game quickly turned from fantasy to harsh reality. As Jack says it best, “Willie Got Me Stoned And Took All My Money.”

Relive The Magic—World Premiere Screening on Maui

Yes you read that right… As you might know, the concert itself sold out in a near instant. Well you’re in luck. The entire event was professionally recorded, and is now being released in what might just be the filmed concert event of the year! This limited theatrical release will feature a selection of the most memorable moments and unforgettable collaborations from the star-studded two-day concert event celebrating Willie Nelson’s milestone 90th birthday.

In fact, the world premiere is taking place this Saturday, June 10th, at the Maui Arts & Cultural Center. Featuring a special in-person introduction from the man himself, this two-hour-plus limited release film will give everyone the opportunity to re-live or experience for the first time this epic event. And I’m not exaggerating in my praise. The event itself is described by USA Today as “headed for the concert history books”. Honoring the legacy of 12-time Grammy Award-winner, the scene at the Hollywood Bowl transcended genres, with the Associated Press remarking: “The parade of partners illustrated one of the night’s themes: Willie brings people together.”

Watch An Exclusive Preview To The Experience

The 90th birthday party show for Willie Nelson at the Hollywood Bowl was a testament to the enduring talent and impact of this iconic musician. The celebration showcased the rich tapestry of his music, brought together an extraordinary ensemble of artists, and highlighted the profound influence Nelson has had on the music industry and beyond. As we reflect on this momentous event, we are reminded of the immeasurable contributions Willie Nelson has made to the world of music and the everlasting legacy he leaves behind for generations to come.

Contact a Maui Real Estate Specialist

Beyond being a trusted advisor in the real estate market, your REALTOR should be a professional who recognizes their role in supporting your wealth building and wealth preservation. Helping to magnify wealth is one of the core values of The Sayles Team; a set of guiding principles for how we serve our clients at the highest level. As experts in the field, we are constantly learning and providing guidance about making the wisest choices for the future. If someone you care about needs guidance or recommendations, please share our contact information and we would be honored to help them!


Dano Sayles R(B)


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