Jagged Little Pill's Derek Klena on Meeting Alanis Morissette and His Obsession with Damn Yankees

Derek Klena is used to playing upstanding men. He made his Broadway debut in 2013 as the heartthrob Fiyero in Wicked. He originated the role of Dmitry, who helps the title heroine rediscover her identity, in Anastasia. Now he’s back on Broadway in Jagged Little Pill, which uses the songs of Alanis Morissette, playing another good-hearted character. In Jagged, Klena’s Nick is the beloved son in the Healy family, who is admitted into Harvard early. Klena admits that as a teenager, he was an overachiever like Nick. “I was a pretty good teenager,” he told Broadway.com’s Beth Stevens in a recent #LiveAtFive appearance. “I was working a lot. I was either playing baseball or doing regional theater shows.”

In Jagged Little Pill, Nick does start off as a golden son but is then faced with an ethical dilemma when he witnesses a crime and doesn’t know whether to report it to the authorities. It’s a tough subject matter, which is why it’s been so gratifying for Klena to see how well audiences have been responding. “The feedback that we've been getting from the audience has been very positive,” he said. “We're affecting people the way that we intended, and we are starting the conversation around a bunch of politically and socially relevant issues, which is the goal. It's just to spark the conversation and encourage communication.” 

Klena grew up in West Covina, California, which was given national prominence as the site of the musical television show Crazy Ex-Girlfriend—note to Rachel Bloom, Klena is ready for the Crazy Ex-Girlfriend stage musical, remarking, “My mom to this day is like, ‘Your agents know you're from there, right? You need to audition for this show because that's kind of where we live.’” As a grade-schooler and a teenager, Klena split his time between playing baseball and doing theater (his first stage role was as a flying monkey in The Wiz when he was six years old). Klena abandoned baseball for acting when he was in college but he still has a dream of combining his two loves: one of his dream projects is to be in the baseball musical Damn Yankees. “That's why I want to do Damn Yankees!” he said. “I feel like I want to play Joe Hardy.”

Not that he’s looking to leave Jagged Little Pill. Klena has played Nick since the musical's first workshops. And he knew the cast had stumbled onto something special when they got the approval from Morissette herself during an early workshop. “Watching how moved she was with the show, and how proud she was of the work that we were doing, was just that kind of a moment we'll never forget,” he said. “And she said that everything that she couldn't really accomplish on the album is now being fully fulfilled on the stage, giving another perspective to the material that she is so proud of. So that meant a lot to us.”

Watch the rest of Klena's #LiveAtFive interview below.