50 Years Ago: Waylon Jennings & Grateful Dead’s Legendary Stadium Show

It’s always a big moment when a big artist plays their first stadium gig. That’s what Waylon Jennings had the honor of doing 50 years ago today—May 26th, 1973—when he took the stage at Kezar Stadium in San Francisco. He wasn’t the featured act though. Waylon was still trying to make a name for himself nationally at the time. But there was no better opportunity to do so than to open a show for The Grateful Dead at Kezar Stadium in 1973, even if the pairing was a bit unusual.

Kezar Stadium had hosted San Francisco 49ers and Oakland Raiders games until 1971. Being situated right near the Haight-Ashbury neighborhood of San Fran, this was The Grateful Dead’s home turf. Also playing the show were West Coast country rockers New Riders of the Purple Sage. The idea was that Waylon’s rock-tinged version of country just may fit with these West Coast rockers that included a little country in their sound.

With The Waylors behind him, Waylon Jennings was at the height of his powers in 1973. Conquering areas outside of Tennessee, Texas, and other country music epicenters to become a national star without the help of Music Row was Waylon’s goal. Waylon’s slick lawyer/manager Neil Reshen was the guy that landed him the huge gig. Reshen was also the guy that got both Waylon and Willie Nelson out of their bad Music Row contracts, and in control of their own destinies, sparking the “Outlaw” movement.

In those days, Waylon used to love to say to crowds at some point early in the show, “My name is Waylon Jennings. We’re all from Nashville, Tennessee, and we play country music. We hope you like it. If you do, I want you to tell everybody you know how much you like it. If you don’t like it, don’t say anything mean about it, because if you ever come to Nashville, we’ll kick your ass.”

Looking at the set list from the show, The Grateful Dead really country’d it up on the day, playing “El Paso” by Marty Robbins, “You Ain’t Woman Enough (To Take My Man)” by Loretta Lynn, and Johnny Cash’s “Big River” among their own more countryfied songs like “Jack Straw,” “Tennessee Jed,” “Me and My Uncle,” and “I Know You Rider.” They played for over four hours, and the bootleg of the show is a cherished item.

Though Waylon called the stadium show Neil Reshen’s “biggest move” and acknowledged it was a “breakthrough moment,” he also relayed in his autobiography, “Musically it didn’t work. Deadheads don’t care if it’s Jesus Christ up there. All they’ve come to see is the Dead. I felt older than them; when I walked out, I probably looked like that sonofabitch who’d told them if they weren’t in by eleven o’clock he was going to ground them. My kids were old enough to be among the crowd.”

In the end though, Waylon says, “It didn’t matter how the shows went, because the word of mouth whispered like wildfire,” and the Kezar Stadium show helped plant a Flying ‘W’ on the West Coast, with folks bragging about being at the legendary pairing of Waylon Jennings and The Grateful Dead for years to come, including some who actually were.

Incidentally, this was not the only show Waylon played with The Grateful Dead. Five years later in 1978, Waylon and Willie were the two biggest things in country music, and The Grateful Dead were one of the biggest live draws in America. They all got together at Arrowhead Stadium in Kansas City to play for a crowd of 80,000. But this time, The Grateful Dead were opening for Waylon. It was no regular opening slot though.

(WARNING: Language)

According to Willie Nelson’s longtime road manager Poodie Locke (RIP), “The Dead played three and a half hours while we watched the clouds building up. This big fucking storm blew in and it was pouring rain when Waylon took the stage. Waylon freaked out. Lightning ain’t the best thing to have happen when you got all this electrical equipment around you. Waylon hadn’t been to sleep in about a year—he just ate Hershey’s Kisses and snorted cocaine. Waylon started hyperventilating. He froze. So Willie walked out on stage, took Waylon’s guitar, and kept on picking.”

But the best part of the story is the exchange Poodie Locke had with The Grateful Dead folks. He told them, “You fuckers played so long you made it rain.”

So they told him back, “Yeah, so why don’t your old man make it stop?”

According to Poodie Locke, as soon as they got Willie’s band set up and he walked out on stage, the rain ended.

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This story has been updated.

Some video from the Kezar Stadium show, 1973:

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