Bryan and the late Marshall Dodge created their humor in a dormitory room at Yale University, and their 1958 album was the first of several that shaped the state's humor and image.
Uttered in exaggerated Down East accents, the jokes have withstood the test of time, including the one about the tourist who befuddled a Mainer by asking for directions. The native concludes with a famous punchline: "Come to think of it, you can't get there from here."
Bryan, who died Wednesday in Sherbrooke, was a native of Long Island, New York, who picked up the local vernacular during summers spent on a lake near Ellsworth, Maine.
The stories often involved a fancy-pants tourist and a laconic Mainer who gets the last word.
"They didn't write from scratch all of these stories. They adapted them. A lot of them were off color, from lumber camps or fishing wharfs. They'd rewrite them. They took them to the next level," said Dean Lunt from Islandport Press, which sells the "Bert and I" albums.
Humorist and storyteller Garrison Keillor recalled playing cuts of the "Bert and I" albums during his early stints as a morning disc jockey. And the original "Bert and I" album made comedian-magician Penn Jillette's list of the top 12 comedy albums of all time.
The pair eventually set off in different directions after selling hundreds of thousands of albums.
Dodge toured the country as a comedian before his death in 1982 in Hawaii, where he was struck by a hit-and-run driver while bicycling.
Bryan, a divinity student who went on to be ordained as an Episcopal priest, used some of his "Bert and I" earnings to buy a float plane. As a bush pilot, he flew his plane to the rugged fishing villages in northern Quebec to minister to local residents.
He created the Quebec-Labrador Foundation with a goal of supporting rural communities and the environment of eastern Canada and New England.
One of Bryan's daughters, Sandy Bryan Weatherall, remembers her dad and Dodge recording stories on a reel-to-reel tape player in her Massachusetts home. And she remembers listening for the sound of his airplane to mark his return home.
She said her dad was a prankster, an optimist and a larger-than-life character whose charisma attracted people.
"He was friends with people from all walks of life. Really, from the bottom to the top, and he believed in them all," she said.
Bryan leaves behind a wife, three daughters, a bunch of grandchildren and a great-granddaughter — and a heap of stories that have withstood the test of time, said Cherie Hoyt, a friend of Bryan's who produced the "Bert and I ... Rebooted" recording with Bryan and Maine humorist Tim Sample.
"You can listen to a good story many times without getting sick of it," Hoyt said. "I know them by heart, but I still find them funny. I still smile. I still chuckle."