Pioneertown was constructed in 1946 as a functional movie Western set — not a studio backlot but an actual inhabitable town, with real buildings on a real desert street, designed to be filmed from any angle. Roy Rogers and Gene Autry were among the investors who saw the value in a permanent outdoor location where westerns could be shot without the logistical complications of building and dismantling sets. The building that would become Pappy & Harriet's was the town's cantina — a social space built into the fiction of the western town, serving the cast and crew between takes. When Hollywood moved on to other locations and other genres, Pioneertown remained, and the cantina found new purposes.

In 1982, Harriet and Claude Allen — Claude went by Pappy — purchased the old cantina and transformed it into a barbecue restaurant and music venue. Pappy died in 1994, and Victoria Williams, a musician associated with the broader artistic community of the high desert, wrote a song called "Happy to Have Known Pappy" as a memorial. Harriet continued running the operation. The combination of BBQ ribs, cold beer, a wooden stage, and an outdoor seating area under the desert sky turned out to be exactly what a certain kind of musician wanted — a place without pretension, with good sound and better atmosphere, at the end of a road that filtered out anyone not specifically trying to get there.

The artists who have played Pappy & Harriet's constitute an unlikely collection for a venue in an unincorporated desert community of a few hundred residents. Paul McCartney performed there — a fact that still seems implausible to people who have not been to Pioneertown and understood the appeal. Robert Plant, whose career runs from Led Zeppelin to Americana folk exploration, has played there. Queens of the Stone Age, the Palm Desert hard rock band, have a deep connection to the high desert community that surrounds the venue. Arctic Monkeys have performed there. André 3000, Patti Smith, and many others have taken that modest stage. Billboard called it one of the top ten hidden gem venues in the United States in 2012. Anthony Bourdain featured it on No Reservations.

In 2003, Harriet Allen sold Pappy & Harriet's to Robyn Celia and Linda Krantz, who operated it for nearly two decades before selling in 2021. Through the ownership transitions, the venue maintained its character — the physical structure, the BBQ menu, the booking philosophy that privileged interesting over famous, and the location that required visitors to want to be there specifically rather than simply passing by. Pioneertown is not on the way to anywhere else. You come to Pioneertown because Pioneertown is the destination, and Pappy & Harriet's is the reason most people make the trip. The movie cowboys who built the town in 1946 would not necessarily recognize what it has become, but the wooden facades and the desert light are still there, just as they left them.