Throwback Thursday Live Music Edition – Willie Nelson’s Outlaw Festival

Growing up, my parents didn’t listen to a lot of popular music of the day (I’m of the age when Willie more obviously fell into that), but Stardust was an album that I can recall. I’m not sure what stood out most – his voice, the mood of the music. Perhaps it’s the simplicity and honesty that makes him accessible. I never overthought it, I just always liked listening to Willie Nelson. Hearing that Willie Nelson’s Outlaw Festival was stopping in Toronto felt like it was time to see the man perform. Bringing artists with him like Terra Lightfoot, Sturgill Simpson and the Tedeschi Trucks Band and coupled with the knowledge that at 85, Nelson doesn’t have many tours left, much less ones up here, made this stop all the more important to catch.

Watching Willie Nelson slowly move to his spot onstage, don Trigger, his stalwart Martin N-20 classical guitar, give a nod to the audience before launching into Johnny Bush’s Whiskey River was a pinnacle moment in my music-loving life. When the day was done and turned to night, it was one thick with the aroma of Willie’s favourite flora and full of more guitar solos than you’d expect, from the precision and melody of Derek Trucks to the scream and shred of Sturgill Simpson to whatever it is exactly that makes Willie Nelson’s playing so unique (it’s in part the Django influence, the incomparable sound of Trigger mixed with Willie’s unusual sense of time). 

But, I’m jumping ahead… While the sun was still, somewhat out, other artists on the bill played to a slightly sparser crowd. Afternoon concerts, especially when not under the blazing sun, can feel light on energy. However, Sturgill Simpson entered the stage to hoots and hollers. His last album, A Sailor’s Guide to Earth was recognized as the best country album of the year in 2017 at the Grammy Awards. The Nashville-based, Kentucky native’s style of country music is often compared the best era of Waylon Jennings career, yet he brings an alternative and even psychedelic lean that draws a wide range of fans. With a set whose length felt just right for a festival slot, it opened with Breakers Roar from Sailor’s Guide, and meandered through cuts mainly from that album, as well as his first two, Metamodern Sounds in Country Music and High Top Mountain. Peppered with a handful of covers, including a better-than-original version of The Promise by Brit one-hit-wonders, When in Rome. I noticed immediately that Simpson had a different band lineup than what I had seen in videos of his live performances. Substituted onstage was keyboardist, Bobby Emmet instead of former lead guitarist, Laur Joamets. Joamets is likely the finest chicken pickin’ guitarist to come out of Estonia. However, the departure proves just how fine Sturgill Simpson is as a guitarist and soloist.

Tedeschi Trucks Band followed with their dozen-large crew. Featuring 2 drummers, horn and vocal sections and the wedded guitarists, the band was the second Grammy winners of the day to take the stage. Susan Tedeschi, known for her searing voice and stolid blues playing, and husband Derek Trucks are the eponymous band leaders. Trucks is justifiably considered not just one of the finest slide guitarists to have ever played, but also one of the overall best guitarists playing today. I knew very little about the band and had only heard a few songs here and there. I assumed that I would spend the majority of their set making article notes and doing research. However, the band was dazzling and easily the finest tuned group I’ve seen in a long while. On occasion, a band this tight looks like they could snooze through a setlist they’ve been playing for the better part of 3 years (I’m looking at you, Hall and Oates), but TTB has enough slack among the polish to give Derek Trucks all the room he wants to sing sweet through his strings. Play as he may, the lyrical style is what shines most. Playing half the set as songs from their previous two studio albums, Let Me Get By and Made Up Mind, the duodecet has scores of covers up their sleeves. Highlighting Tedeschi’s Janis Joplin and Bonnie Raitt tones, the set’s cover of John Prine’s Angel Of Montgomery was a highlight, particularly mashed up with the Jerry Garcia tune, Sugaree. By mid-set, the venue looked to be at capacity. Closing with the soulful Billy Taylor jazz-gospel song, I Wish I Knew How It Would Feel To Be Free. This number gave vocal section star, Mike Mattison a chance to step into the spotlight and put his pipes up to measure with Trucks’ guitar. Ending on this high note as the sun dropped, I had another walk around the venue to take measure.

Where many seats were empty during the day, any fear that Willie Nelson would be performing to a less-than-packed house were quickly dispelled. Each seat was now taken, despite the night being the colder than any since the spring. I wondered if the cold day may keep folks at home – it was cold enough that performers were wearing heavy jackets and toques and guitarists could be seen blowing on their fingers. But to state it again, the prevailing spirit seems to be that when Willie comes to town, you go see him. No amount of cold or indifference should prevent a music lover from paying respects to an artist and songwriter responsible for some of the finest music ever, country or not. This was evidenced by just looking at the crowd. Willie’s demographic is frankly, eight months to eighty years old, with the aisles supporting an equal measure of strollers and walkers. I’ve seen no truer display of an all-ages show.

Soon enough, a Texas state flag the size of an Olympic-sized swimming pool dropped behind the stage as Willie came out to a roar of cheers. Accompanied by his Family band, including ‘little sister’ Bobby on piano, son Micah and longstanding roadmates, Mickey Raphael on harmonica, and Paul English on drums. He smiled as he strapped on Trigger and launched right into Whiskey River, quickly followed up by Still Is Still Moving to Me. Without delay, he soon told us we were about to hear a ‘little Waylon’ as he played the first hit of the night, Good Hearted Woman. While many of Nelson’s hits are actually covers (which he’s made his own), a quick medley included one of his most famous songs made so by Patsy Cline. Crazy was thrown in between Funny How Time Slips Away and Night Life. Keeping the set tight, Willie said few words to the audience, making sure he still had time for his own hits, including Angel Flying Too Close to the Ground, Roll Me Up and Smoke Me When I Die and On the Road Again. While static onstage, Nelson looked spry as he adroitly flung hats and bandanas out into the audience. Willie’s set ended with Will The Circle Be Unbroken joined by Tedeschi and Trucks and I’ll Fly Away. With a wave to the standing crowd, Willie left the stage, likely off to board his bio-diesel bus, Honeysuckle Rose to get on the road again.

There has never been an artist like Willie Nelson, much less an artist in country music. Where at present, it’s a bland slurry of shaking moneymakers, crushing cold beers, Flag-above-all politics, trucks and tequila that’s trending in the country scene. It’s an overproduced mess of vapid pop masked with an exaggerated twang, a generic acoustic sheen and a 4-beat stomp. No other genre of music has declined from its roots to such a soulless shadow of itself. So, to see an originator like Willie Nelson, one of the last outlaw country artists, as prolific as ever and as real as fuck, out there, touring and being as political as these times require, offers hope and inspiration. Since growing his hair out in the 70s, Nelson has marched only to his own beat and happily tossed up a middle finger to whomever would attempt to admonish. An outlaw in the scene, he’s had his share of legal problems from pot busts to tax hassles. He’s been an activist for many years, for many issues, most prominently farming families (helped through his creation of Farm Aid back in 1985), but also putting the spotlight on marijuana legalization, bio-fuels, animal welfare and as a vocal supporter of LGBT rights. Willie’s been spreading the word about Grassroots Leadership in their Hutto Community Deportation Defense & Bond Fund to help make release reunification plausible for women detained in the USA’s only all-female detention center for asylum seekers. And just a couple of weeks ago, Nelson headlined a concert in support of Texas Senate candidate, Beto O’Rourke

At 85, Willie Nelson has had a remarkable career and life. While there’s no doubt the Red-Headed Stranger is moving a bit slower in these later years, it would be hard to tell without looking hard. Since 2016, he’s released 5 albums, played over 200 shows, appeared in 2 movies and launched his marijuana brand. As he closes 2018 with a couple dozen more shows, he’s showing no signs of slowing down, much less stopping. So, Willie, keep strong and we’ll see you on Outlaw Fest 2019!

Aron Harris

Aron Harris

Music Editor at Addicted
Aron Harris is Addicted's music editor as well as a designer/photographer/writer. Aron can be found on Instagram at for photography. As well, @dadrockdad for his dad blog.
Aron Harris

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