The Second City Training Center was thrilled to welcome a house full of students to participate in a Q&A session with Chris Henchy, a member of The Second City’s board of directors. Henchy is a versatile writer, producer, and director who was a partner of Gary Sanchez Productions and a co-founder of legendary comedy site Funny or Die. A writer and producer on network shows including Spin City, Eastbound & Down, Entourage, and I’m With Her (inspired by his own real-life marriage to Brooke Shields), he also wrote the feature films Land of the Lost (starring Will Ferrell), The Other Guys (starring Ferrell and Mark Wahlberg), and The Campaign (starring Ferrell and Zach Galifianakis). Henchy produced the feature films Tammy, The Boss, Get Hard, Daddy’s Home and Daddy’s Home 2. He made his directorial debut in 2020 with Impractical Jokers: The Movie, which he also wrote and produced.
The Q&A, led by Artistic Director for The Second City Toronto Training Centre Julie Dumais Osborne, allowed Henchy to impart his industry wisdom and experience to an eager crowd in Donny’s Skybox.
From Wall Street to Hollywood
Henchy began by explaining his non-traditional route into the comedy world. After studying finance in college, he moved to New York with the intention of pursuing comedy—but was hired on Wall Street. “I was not good,” the failed financier admitted. Henchy began immersing himself in the stand-up world, ultimately selling his first joke for $150. That small win was enough to call his family and inform them he’d made it, and there was no turning back. He began writing, writing, and writing, following the unanimous advice he received to “keep writing, and then write some more.” So how’d he get people to read all that writing? By “banging on doors until someone said ‘okay.’” Persistence pays off.
Learning from the Best
In 2007, Henchy co-founded revolutionary comedy site Funny or Die with partners Will Ferrell and Second City alum Adam McKay. The site’s debut original short, “The Landlord,” went viral immediately (to date, it has over 84 million views) and sealed an early success for the platform, which expanded to include a TV and film production company before the founders sold it earlier this year. “It was a really great run,” reflected Henchy, grossly understating the influence that FoD had on bringing short-form comedy to social media in an era long predating TikTok.
Henchy’s collaborations with improv superheroes like Zach Galifianakis and Melissa McCarthy, in addition to Ferrell and McKay, have served him well. “I was surrounded by people who grew up in the improv world…I had on the job training. And I learned from two of the best.” A lot of his skill set grew from being open to learning as he went, and he advised that might not be the best route to take. When asked about his experience as a creative producer, Henchy admitted, “It took me years to learn, but you’ll learn it here,” noting that a program like the Second City Training Center offers students hands-on opportunities to become a strong, well-rounded creatives from the get-go.
Burning Questions, Answered
Henchy addressed the many, many questions in the room—as well as fielding more during a virtual Q&A that was held immediately following the in-person session. Here is just some of the guidance he offered up.
What makes a successful writers’ room? Likening a writers’ room to a football team, Henchy says the right mix has “steely veterans” as well as new voices. “You create a good team. When it works, it’s amazing.”
What is the secret weapon of comedy writing? “Writing alts.”
When trying to break into the business, when is it okay to ask a friend for a favor, and when is it stepping beyond the bounds? “Bet on yourself, and always ask.”
Is there a project he regrets saying no to? Admitting there are some projects he regrets saying yes to, Henchy advised “work begets work.” You never know what one project might lead to or what connection will reveal itself.
How do you envision the future of comedy? Looking forward to a more diverse future and broader landscape, Henchy relied on his favorite boat metaphor to illustrate how the success of others isn’t something to envy—it’s something to celebrate. “You’re rooting for everyone to do well,” he said. “A rising tide raises all ships.”
And finally…as a writer and a creative spirit, how do you force yourself to let go and “be done” with a draft? “Fuck deadlines.”
Well said, Chris Henchy. We think you’re going to fit in well here at The Second City.
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