Think back to the ringing guitars, the spinners, the patchouli oil and the haze of pot smoke hanging over an arena – the psychedelic country rock of Grateful Dead concerts seem like an unlikely cradle for today’s conservative commentators.

And yet, 10 years to the day after Jerry Garcia’s death on August 9, 1995, no less than three of Generation X’s most high-profile young conservatives remain dedicated Deadheads: Deroy Murdock, Tucker Carlson, and Ann Coulter.

This perhaps unexpected fact highlights the stark gap between the stereotype of the crew-cutted, humorless, Muzak-listening conservative of the past and the libertarian-leaning conservatives who came of age during the Reagan era.

It’s easy to forget that the highest grossing touring act of the 1980s was not some spiked-hair, synthesizer duo, but the Grateful Dead. Their seemingly perpetual concert tour was the equivalent of joining the circus, a quintessentially American rite of passage. The smiling bearded visage of Jerry Garcia was as much a marker of day-to-day life in the times as the reassuring presence of Reagan’s square jaw and pompadour in the White House. And so perhaps it’s not surprising that the children of Reagan and Garcia grew up to be internally noncontradictory amalgams of both influences.

Deroy Murdock, a nationally syndicated columnist and contributing editor with National Review Online, is also a veteran of 69 Grateful Dead concerts, by his count. “It’s easy to reconcile my affection and admiration for Ronald Reagan and Jerry Garcia: They both were committed to individual freedom,” Mr. Murdock attests. “The patriotism and love of country that Reagan embodied, Garcia also reflected. I remember the sole American flag waving on top of the stage at outdoor Grateful Dead shows as well as the patriotic lyrics, with their iconography of the Old West: cowboys, gambling in saloons, and steam trains crossing the prairies.”

The primary overlap from adolescent enthusiasm into adult ideology seems to be in the common ground of libertarianism. “My two favorite definitions of libertarianism come from P.J. O’Rourke and Jerry Garcia,” Mr. Murdock says. “As P.J. put it, ‘Make a right at taxes. Make a left at Sex. And straight ahead is paradise.’ When Garcia was asked how Deadheads should behave at the band’s concerts, he said, ‘Do what you want, man. Just don’t stand on anybody’s head.’ This just happens to parallel the Golden Rule, ‘Do unto others as you would have them do unto you.'”

Tucker Carlson, who now hosts a nightly show, “The Situation,” on MSNBC, is a veteran of more than 50 Grateful Dead concerts and still listens to the Dead every day at home with his wife and children. “Following the Grateful Dead was one of the last structured-but-wild things you could do in America, at least when I was in high school and college,” Mr. Carlson said. “I always liked how apolitical the band was, at least in public. Garcia’s position seemed to be: ‘We’re just musicians. We’re not here to tell you what to do or how to think.’ He was totally opposed to lectures – giving or receiving them. He was the opposite of the self-righteous liberals who ran the schools I went to.”

This seems to hit on a second major point that can explain the thriving existence of Jerry Garcia’s conservative children. The rigid humorlessness of the politically correct crowd during the 1980s and 1990s was one of the right wing’s greatest recruiting tools. The evolution of the American left-wing from “We Shall Overcome,” peace-and-love advocates to angry, blame-America-first guilt mongers had the effect of turning campus liberals into the mirror image of the uptight conventional conservatives of the 1950s and 1960s. It became rebellious to resist their influence: reading Hunter S. Thompson led to appreciating P.J. O’Rourke; attending a Dead show and admiring Ronald Reagan were not contradictory. The optimistic “live and let live” atmosphere of Grateful Dead shows were a welcome asylum from the increasingly personal attacks levied on college campuses during the height of the culture wars.

But as George Will once said, “The four most important words in politics are, ‘up to a point,’ ” and this trend of enthusiastic, conservative Grateful Dead aficionados has its logical limits. Ann Coulter is fond of pointing out her love for the Grateful Dead as a way of disarming critics, but it is tough to imagine how Jerry Garcia would appreciate her book-length defense of Joseph McCarthy. Likewise, her comment to a Salon.com interviewer who asked, “So it’s up to the community to decide whether or not to burn queers in the public square?” – Ms. Coulter replied, “Right. That preserved the maximum freedom” – doesn’t exactly reek of “live and let live” libertarianism. Nonetheless, Ms. Coulter counts herself a fan, and all the protests in the world can’t erase that fact.

Ten years to the day after his death, the influence of Jerry Garcia and the Grateful Dead live on, in wide and improbable circles. Especially in a time of increasingly rigid political partisanship, it’s perhaps helpful to recognize that personal experience and superficial political assumptions can sometimes be at odds – the book cover does not tell the whole story. One of the enduring, if unexpected, lessons of Jerry Garcia’s life is as apple-pie American as it gets: We’d all get along a lot better if we refocused on Thomas Jefferson’s founding promise of life, liberty, and the pursuit of happiness.