Is there a more beloved icon in America today than Willie Nelson? He’s like your cool, pot-smoking grandpa who’s as quick to bust out a tearjerker of song as he is to warm your heart with an infectious laugh. It’s the reason he remains the only 84-year old going who can continuously pack them in at 20,000 seat-plus outdoor amphitheaters in nearly every town in the country. This summer, some of Willie’s biggest fans and oldest friends have joined up with him once again for his Outlaw Music Festival, an OG Lollapalooza-type touring event. The tour features a shifting lineup of some of the most vital, and important country music artists in the game today seeking to one-up each other on a nightly basis.
I caught the show this last weekend at Summerfest in Milwaukee, Wisconsin. On the bill that evening was Lukas Nelson -– Willie’s son -– Margo Price, Nathaniel Rateliff, Jason Isbell, Sheryl Crow, Willie, and just before him, Bob freaking Dylan. The entire thing is a nine hour long continuous marathon of music that never really wears down. It was a perfectly paced mix of country music’s past, it’s present and a small glimpse into its future. While everyone on the bill brought their A-game, some folks burned just a little bit brighter than the others. Here’s a ranking of the best performances I saw.