While The Rolling Stones may be the world’s greatest rock ‘n’ roll band, The Grateful Dead are the world’s greatest touring band. Playing nearly 3000 shows to over 25 million fans over five decades certainly gives them legitimate “street cred” as the most prolific live act of all time.

Their music changed the face of a generation and they inspired an entire genre of psychedelic musicians to follow. One might wonder how the former house band for Ken Kesey’s Electric Kool Aid Acid Tests generated such a dedicated following, but the answer is quite simple: their music was inspirational and it spoke to the soul. The Grateful Dead weren’t just a bunch of long-haired vegans with a fix for psychedelic fungi, they had some real wisdom to share. But it was only after the former jug band and their bluegrass and rockabilly sound became transformed by the profound lyrics of songwriter Robert Hunter that The Grateful Dead achieved true greatness.

As a clinical psychiatrist and an academic writer who’s explored The Grateful Dead on multiple levels, I can tell you from the things that folks have shared with me that I’m not the only one who finds their songs to be tremendously insightful. But as a second-generation Grateful Yid with scores of concerts under my belt, I can also say that The Grateful Dead’s music reached me on a spiritual level.

In honor of The Grateful Dead’s 50th Anniversary “Fare Thee Well” Goodbye Tour featuring the surviving band members and a few guest stars, it is fitting to explore how their songs carry a wisdom that penetrates the Jewish soul. (Let’s not forget that their drummer, Mickey Hart, and promoter, Bill Graham, were both unabashedly proud Jews, which can’t hurt.)

I realize that this might seem like kind of a stretch, but this is a band who routinely played a song called Samson and Delilah and whose tune Fire on The Mountain is clearly referring to Mount Sinai. The poetry of The Grateful Dead lends itself to explication and with this caveat, here is my list of the Top Five Dead lyrics carrying a message that touches the deepest realms of the Jewish soul…

  1. Deal—“If I told you all that went down it would burn off both your ears. To me, these words capture the essence of the Jewish story. Could anyone really imagine that that Jews would still be standing thousands of years after the world’s greatest empires remain only in history classes? As Mark Twain once wrote, “The Egyptian, the Babylonian, and the Persian rose, filled the planet with sound and splendor, then faded to dream-stuff and passed away; the Greek and the Roman followed; and made a vast noise, and they are gone; other people have sprung up and held their torch high for a time, but it burned out, and they sit in twilight now, or have vanished. The Jew saw them all, beat them all, and is now what he always was.” History was stacked against us but we’re still alive and kicking…put that in your pipe and smoke it Hamas!

  2. New Speedway Boogie—“One way or another this darkness got to give.As experts in the waiting game, we Jews are always preparing for the beautiful moment of redemption when our hardships will become only a memory. This is a profound reminder of what King David wrote in Psalm 126, “Those who sow in tears will reap with songs of joy.”

  3. Help on the Way—“Without love in the dream it will never come true.” Maimonides wrote that fear of Heaven is a lower level of divine service and that loving God is the loftier spiritual quest. As Rabbi Noah Weinberg of blessed memory taught us, God created us because he loves us and wants us to get to the ultimate pleasures attained through the path of the Torah. With love, His vision of the universe is coming true.

  4. Broke-Down Palace—“Fare you well, fare you well, I love you more than words can tell.” Anyone who has ever had the experience of praying at the Western Wall also knows the indescribable feeling of heart-breaking loss that must be endured when leaving our nation’s holiest place. In truth there are no words to express how powerful it is to be there and how crushing it is to go. This line certainly captures the essence of spiritual yearning as described by King David in Psalm 137, “If I forget you O’ Jerusalem.”

  5. Tennessee Jed—“Tennessee, Tennessee, there ain't no place I’d rather be.” As soon as we leave Jerusalem we yearn to go back. Much like the forsaken character from this song, no matter how good things might be, every Jew knows how badly they wish to return to our national homeland’s capital city. As Rabbi Judah Halevi wrote over a thousand years ago, “Though I am in the West, my heart is in the East.”

If there was room for a sixth we could find Rebbe Nachman of Breslov’s famous quote “It’s a tremendous mitzvah to always be happy” alluded to in the song He’s Gone which contains the lyrics, “Nothing left to do but smile, smile, smile.”

“Keep on truckin’!”