Alan Cumming + Cyndi Lauper

When Studio 360 asked Alan Cummingto choose an interview guest, his first choice was one of the great pop stars of our time, his friendCyndi Lauper. They got to know each other when they starred together in “The Threepenny Opera”on Broadway in 2006 (he was Mack the Knife, she was Pirate Jenny). Like the rest of us, Cumming has been amazed by the many turns Lauper’s life and career have taken.

Lauper broke very, very big with her debut album in 1983,“She’s So Unusual.” It came out at the same time as Madonna’s self-titled debut and the two were pitted against each other by their record companies. Lauper hated the trumped-up rivalry. “First of all, I liked her,” Lauper tells Cumming, “and, second of all, it’s another woman. Sisterhood is a powerful thing.” The rivalry left Lauper even more insecure. “I always tried harder because I didn’t think it would be good enough,” she explains. “I always felt like The Little Engine That Could.”

She’s keenly felt that her chirpy voice and New York accent colored what people expected of her. But she’s been undaunted. “Every time you’re stopping me with your gatekeepers, I’m gonna show up some place else and say ‘Ooh look now I’m here! Think you can stop me now?'”

Her records have hit on everything from synth pop to acoustic music toelectronic danceto blues — her latest, “Detour,” is a country album recorded in Nashville. In 2013, she became the first woman to win the Tony Award for Best Original Score for the musical“Kinky Boots.” And she’s been a longtime champion of LGBT rights, organizing concert tours and starting her own foundation, theTrue Colors Fund. At 62, Lauper shows no signs of slowing down. “I guess I like to be alive,” she says.

(Originally aired September 19, 2014)

Cyndi Lauper and Alan Cumming backstage at the 2006 Tony Awards

(Photo by KMazur/WireImage for Tony Awards Productions)

Bonus Track: Alan Cumming’s extended conversation with Cyndi Lauper