Inside Tosca Cafe, a 96-year-old San Francisco bar where the ambience is perpetually dim and the white-shirted bartenders mix cocktails with affected names like the “Oaxacan Firing Squad” and the “White Nun,” Levi’s President James Curleigh—he goes by “J.C.”—is telling a story about the night when actor Sean Penn (who helped save the bar in 2004) shot a hole in the wall. According to J.C., Kid Rock was hanging out in an alcove above the kitchen that had been fashioned into a private V.I.P. room, intermittently strumming an acoustic guitar. Penn arrived later, and an altercation occurred that led to the Oscar-winning actor firing his pistol into the otherwise-empty restaurant floor below, leaving a small .22-caliber bullet hole underneath one of the paintings hanging in the main dining room.

J.C. talks about hanging out in that same room more recently with Florence Welch, of Florence and the Machine. When he talks about Tosca Cafe and why it’s one of his post-work watering holes of choice, it becomes apparent that it isn’t about the celebrities that hang out here or the preferential treatment he gets as a regular, it’s because of the undeniable authenticity it offers that Curleigh can’t quite find anywhere else.

When Curleigh joined Levi’s in July 2012, he was instrumental in channelling the Levi’s brand’s heritage to differentiate the company from its competitors. His biggest move thus far? Facilitating Levi’s purchase of the naming rights to the new stadium of the San Francisco 49ers in 2013. The recently christened Levi’s Stadium is set to host Super Bowl 50 in February, which will propel the Levi’s brand name to 100 million-plus viewers.

Before that, Levi’s Stadium will host an eclectic lineup of concerts, ranging from One Direction, to Taylor Swift, to the surviving members of the Grateful Dead. As a child of the ’60s, music is especially important to the 49-year-old Curleigh, and in many ways it’s intrinsic to how he views the brand.

“That notion of ‘living in Levi’s’ has been with me all my life,” he says.

J.C. was born in Nova Scotia to a Canadian Navy helicopter pilot and a mother he describes as a “free spirit.” He remembers wearing Levi’s since he was 6 years old. In particular, he remembers the white Levi’s corduroy pants he wore at his eighth-grade graduation, and the Levi’s cut-off shorts he wore at 16, when he and his brother went on a backpacking trip in Europe with nothing but a Europass train ticket and the money in their pockets.