A 91-year-old Willie Nelson slowly saunters onstage wearing a black puffer jacket for a chilly early September evening at the Tinley Park, Illinois, Credit Union 1 Amphitheatre. He greets the crowd gently, his signature braids hidden beneath a white cowboy hat. A man who has played countless shows, he looks at home on stage, his beloved guitar Trigger guitar in hand. The hole he’s scratched in its body is plainly in view.

Years ago, Nelson said all he wanted to do with his life was tour and play music with his friends and family, and that’s exactly what he’s done. Every year, he hits the road for months with a lineup of renowned and up-and-coming practitioners of folk, country and rock. This year, the Outlaw Music Festival featured a rotating lineup of Nelson and Family, Bob Dylan, John Mellencamp, Robert Plant and Alison Krauss, Billy Strings, Brittany Spencer, Celisse and Southern Avenue.  

The festival, which took place last Saturday, brought the largest crowd I’ve seen at Credit Union 1—a sea of folks in cowboy boots, American flag bandanas and worn-out jeans, with coats and winter hats layered on top. And it speaks to the legendary status of the lineup. But it’s a show people attend to see those big-name musicians, not to see incredible performances.

Mr. Outlaw

Nelson, who had his first two singles—The Storm has Just Begun and When I’ve Sung My Last Hillbilly Song—come out in 1955, spearheaded the outlaw country subgenre developed in the 1960s as a reaction to conservative restrictions of the Nashville Sound. According to Billboard magazine, he’s scored 18 No. 1 Hits and 53 Top 10 Hits across a discography spanning 152 studio albums (which includes live albums, compilations and soundtracks).  

He’s a 12-time Grammy winner and has had 57 nominations. His worldwide album sales surpass 60 million, and he’s consistently releasing new music. Nelson’s latest album, The Border, just came out in May of this year.  

With a career spanning hits that include Mammas Don’t Let Your Babies Grow Up To Be Cowboys, On The Road Again, Highway Man, Always On My Mind and Good Hearted Woman, Nelson smoothly rolls through the songs with ease. His deep bass voice holds strong in his later years, echoing into the open-air amphitheater.   

Nelson is one of the most intricate guitar players in country and rock music combined, and his long boney fingers still swiftly strum in rhythm. In his 10th decade, he doesn’t sing and play the way he used to, though. When he needs moments to catch his breath, Waylon Payne—son of Jody Payne—takes over the melodies and plays rhythm acoustic guitar.  

It’s a sweet performance that forced images of his career to flash across my mind. Nelson is a legend, who will likely keep playing shows until he no longer can, and to see him enjoy the life he leads through music is nothing short of magical.

Tambourine Man

Bob Dylan, 83, paved the way for folk singer-songwriters to earn mainstream appeal and pioneered the ‘60s spirit of protest. Dylan set a poetic lyrical standard for his successors that earned him a Nobel prize for Literature in 2016. A biopic on his early career is coming out this December starring Timothee Chalamet.  

He’s released 30 studio albums and a long list of live albums and compilations, winning 10 Grammy awards after receiving 38 nominations. With more than 125 million global record sales, he’s had nine albums reach No. 1 on the Billboard charts.  

Dylan’s roster of hit songs includes Blowin’ In The Wind, Mr. Tambourine Man, Like a Rolling Stone, Hurricane, and Knockin’ On Heaven’s Door—yet, he didn’t play a single one of them live. I was excited to see him in person. But truly, there wasn’t much to see.  

In his live performances today, it’s nearly impossible to hear what Dylan is singing—his signature style of mumbling is amped up a few notches and it just sounds like he’s humming. And while I didn’t expect to know every song he played, I truly couldn’t name one. It could have been a Bob Dylan impersonator up there for all I knew.  

All I could think about was what he was like as a performer early on in his career—how I would kill to go back in time to see him in his prime.  

Hiding behind his piano, Dylan turned around after each song, addressing the crowd only when he bowed at the end of his performance. Afterward, I looked around in confusion. Was that really … it?  

But, hey, at least one day I can tell my kids I got to see him live, right?

Small town rocker

John Mellencamp was the performer I was least excited to see, and he ended up my favorite of the night. He’s the Midwestern version of Bruce Springsteen, only you can understand what he’s singing a bit more.  

At 72, Mellencamp had energy and a large band backing him up. He’s known for heartland rock and manifested a warm summer Midwest vibe.  

During his hit song Jack and Diane, he let the crowd sing the words after the first verse. But instead of singing the second verse, folks in the front row apparently started singing the chorus.  

“Hold up,” Mellencamp said. “I wrote this song when I was 25 and spent all day working on a second verse. And people still don’t know it!”

He laughed and plunged into the lyrics.

Suckin’ on a chili dog outside the Tastee Freez / Diane’s sittin’ on Jackie’s lap, he’s got his hands between her knees / Jackie says, “Hey Diane, lets run off behind a shady tree / Dribble off those Bobby Brooks slacks and do what I please.”

Though I knew all the words, it was a hilarious refresher.  

The Outlaw Music Festival is rounding out the tour with shows in Ohio, Pennsylvania, Michigan, New York and New Hampshire.  

If you haven’t heard Willie Nelson’s newest music, start with his song Once Upon A Yesterday. It’s a soft acoustic ballad that will lull you into tranquility.

Pay attention to Nelson’s voice. Musician’s vocals are typically their biggest change as they get older. But Nelson’s voice doesn’t falter. He maintains a soft approach and doesn’t use a crazy range. But keeping it simple is just as good.