The Oklahoma Route 66 Association recently announced that its 2026 Route 66 centennial T-shirt features artwork from late Route 66 artist Bob Waldmire.
Waldmire, a well-traveled hippie whose intricate pen-and-ink drawings were beloved by the Route 66 community, was also the inspiration for Fillmore the Volkswagen minibus in Disney-Pixar’s 2006 “Cars” film.
He was also the son of Ed Waldmire, who founded the iconic Cozy Dog Drive-In restaurant along Route 66 in Springfield, Illinois.
Bob Waldmire died of cancer in 2009 at age 64.
The association stated this about the Waldmire shirts:
“Bob created a series of drawings in 1989 featuring landmarks along Oklahoma Route 66,” said Association President Rhys Martin. “We felt this would be a wonderful way to acknowledge the road’s history while reminding folks that the journey continues. We’re very grateful to the Waldmire family for allowing us to honor his legacy as we celebrate the road’s 100th anniversary.”
The new design features some artwork never before seen, such as a sketch of downtown Canute that was part of a postcard that was not finished before Bob passed away in 2009.
The front of the shirt even has a 100th-birthday message … but where did that come from?
“When Bob created a new piece of art and wanted to include something he’d already sketched, he would photocopy it, cut it out, and paste it together. With permission from the Waldmire family, we did the exact same thing,” said Martin.
The Association’s archives included a sketch Bob had created for the 66th anniversary of Route 66 in 1992; that was combined with a bit of his handwriting to create the number 100.
“It’s authentic Bob Waldmire in multiple ways.”
Shirts can be purchased online here and in person at the association’s booth inside the Meadow Gold Mack Route 66 Outpost in Tulsa.
More Waldmire art can be seen and purchased here.
(Image of the Oklahoma Route 66 Association official centennial T-shirt featuring Bob Waldmire drawings)