Kal Penn tries on several hats in life — and looks good in them, too

Shreya Ranganath connected with Penn after his appearance at the L.A. Times Festival of Books for an exclusive conversation about his seriously funny new memoir, “You Can’t Be Serious.”

A bright blue book cover featuring Kal Penn looking into the camera as different hands adjust his clothing, fix his hair, and put on makeup.

Above all, Kal Penn hopes that you laugh.

This single goal has molded his career, from playing the Tin Man in his eighth grade musical, “The Wiz,” to starring as one half of the lovable duo in the hit comedy “Harold and Kumar Go to White Castle.” Now, it has guided him onward to his next venture: Writing a hilarious, yet tender memoir sharing some of his most memorable experiences as a multihyphenate.

Penn brought his energy to the L.A. Times Festival of Books stage, where lines of people stood eagerly awaiting his signature after selling out all copies of the book present at the event. It was clear that the actor’s love for laughter was contagious to the crowd.

Penn was direct about where his love for acting stemmed from. In a time when racial representation on screen was still in its infancy, he named his high school drama club experiences and Mira Nair’s film, “Mississippi Masala,” as his main influences. Seeing Denzel Washington and Sarita Choudhury playing characters that weren’t two-dimensional and didn’t fall into traditional stereotypes was a brand new concept to him.

“They [made] mistakes, they [fell] in love, and they [did] all of the things you expect[ed] on-screen characters to do,” Penn said. “I thought, ‘If these people could do this, maybe I could too.’ That’s when I realized I wanted to [act] for the rest of my life.”

Penn’s enthusiasm for storytelling and success with acting prompted some questions about the timing of this memoir. What made this story important now? Penn recalled considering the same point with his manager early in the writing process. He didn’t feel his personal story was one worth telling.

“My manager was like, ‘Hey, you should write a book.’ And I asked, ‘Why?’” said Penn. According to his manager, nobody had gone from working in Hollywood to working in politics. “I retorted, ‘Literally, the governor was Arnold Schwarzenegger.’”

It took Penn thinking about his various career ventures, from White Castle to the White House, to realize the value of lives that don’t follow just one path. He aspired to write this book for the 23-year-old version of himself, who, much like those who faced unemployment and uncertainty during the pandemic, struggled with the idea that he could have multiple passions. With “You Can’t Be Serious,” Penn aimed to debunk the idea that people “have to pick one thing and stick to it.”

“Systems can change over time and your life can have more than one journey,” Penn said. “It seems like people are finally finding that balance in life that I feel so grateful to have experienced. I want to share my story. It feels like the right time.”

Although Penn has entertained audiences on screen for years and is no stranger to scriptwriting, dipping his toes into personal narrative was a different ballgame.

“I remember thinking: Why am I feeling the same insecurity I felt when I was in the seventh grade when I’m writing these stories?” Penn recalled.

Penn believed that putting to paper the stories he had told buddies for years helped him find his unique voice. As evident by his multi-tiered career cake, which included a two-year sabbatical from acting to join the Obama Administration, Penn has always embraced the unknown and gravitated toward positions where he can be of service.

His service to the community became more impactful when recalling the root motivation behind his hard work: A wish to see more people who looked like him on screen growing up.

“When you don’t see it, it’s almost like your real world opportunities are limited. And maybe [it seems like] you don’t have every opportunity in the world,” Penn said. “But that’s not true. You do. You just have to work harder for it.”

Penn left younger generations with advice for how he deals with the working world.

“If I’m entering a field where I have to work ten times harder, yeah, it’s not fair, but I better work ten times harder and hope that it ultimately changes the system for somebody else down the line, too,” he said.

Flash forward to a successful Penn at the Festival of Books’ main stage, owning his story like he’s the same bright-eyed actor back in the theater classes of his youth. A sea of faces cheered at his experiences and marveled at his authenticity.

“At the end of the day, I just hope you laugh,” Penn said. “I hope you just laugh and enjoy [the book] for the purpose of the storytelling, knowing we all have multiple paths, passions and interests.”