A series exploring how risk shapes our decisions.
Picture yourself on a tightrope, suspended over the abyss. Your mission? Reach the other side without plummeting to your doom—unless, of course, you count the not-so-soft net below. That’s precisely what attempting comedy feels like, according to Will Burke, a distinguished Harvard alumnus and a nearly two-decade veteran of the “Jimmy Kimmel Live!” crew. Though the safety net isn’t soft, it certainly has its perks—like a free ticket to the circus!
“The moment you step on stage, it’s like walking a tightrope,” Burke mused. “You’re gambling with your timing, your perspective, and at times, your dignity, all for the slim chance of inducing a laugh.” Enjoyable, isn’t it? A high-stakes game show where the prize is either laughter or a symphony of crickets chirping in solidarity.
Burke’s pursuit of humor kicked off as a class clown in the hallowed halls of New England prep schools—presumably while dodging the occasional lecture from his father, a teacher. His comedic journey continued at Harvard’s improv troupe, On Thin Ice, and a Shakespeare outfit he had the audacity to establish. Then came Hollywood, where he became well-versed in the art of “waiting for your career to take off” while serving drinks and wiping up after others’ spills.
While some envision a life of laughs as the ultimate dream, Burke would nod knowingly—because it’s more like a rollercoaster of risk. There’s the danger of creative exposure, the peril of overstepping comedic boundaries, and who could forget the ever-looming fear of being “that funny guy” who doesn’t make it big? “The grandest risk was trading my Harvard diploma for the dive bars of Hollywood,” Burke lamented, “as if I willingly leaped from the Ivy Tower right into the fishbowl.”
Sure, a Harvard degree has its perks, but as Burke discovered upon moving to Los Angeles in ’99, it’s not exactly a VIP pass to the small screen. “I had to navigate the same grimy open mics, kut-15 auditions, and acting classes as every other aspiring comedian. My side hustle? Juggling bartending, tutoring, catering, and of course, cracking jokes,” he explained, presumably while sipping on a cocktail of irony.
After a grueling decade of auditions and rejections that could make Job look like he had it easy, Burke almost settled for a corporate gig back in Boston. “I effectively said yes to a bank job, surrounded by 401K pamphlets and the smell of responsibility. It felt responsible—until fate elbowed me in the ribs.” And just like that, Burke flew back to LA, where the stars aligned, and he was offered a role writing for “Jimmy Kimmel Live!” Twenty years later, he’s still there, dodging the shakily swinging ax of comedy showmanship.
Each day at “Kimmel” is a risk, akin to walking a tightrope while juggling chainsaws. “Some days, I was convinced my desk would be cleared before lunch,” Burke shared. “You get to see the unfortunate drama: writers getting ousted. One moment, they’re the kings of comedy, and the next, it’s like, ‘Hey, where did that guy go?’ Real-world pressure, my friends, much like trying to be the funniest one at a family reunion without getting cornered by Uncle Bob.
When the inevitable rejection in the writers’ room looms, Burke navigates his emotions like a pro tightrope walker. “It’s impossible not to take things to heart,” he admitted, “but here’s the trick: walk in thinking you’re the only one who can play this role and leave convinced you’re the worst. This way, your disappointment is preemptively mitigated, like a financial investment in emotional stability. What a humorous paradox!
In his private life, Burke embraces the risky side of humor. “Comedy can dissolve tension. It’s the social lubricant we didn’t know we needed, especially when you’re the outsider,” he quipped. “And sometimes, dropping an inappropriate joke at a fancy dinner party is just what the doctor ordered.” Naturally, there’s always the chance of crossing a line. “Picture this: strutting downstairs with a bra on your head at a party where you don’t personally know the occupants. Yeah, that’s the line, folks!”
But at the end of the day, it seems the potential for laughter far outweighs the risks of embarrassment or tumbling off that tightrope. “This job? It’s a dream,” Burke concluded, “the kind of wild journey I envisioned as a kid watching shows like ‘Saturday Night Live’ or ‘The Muppet Show.’ There’s chaos backstage, and every day is an adventure—complete with Stormtroopers and flying chickens. What more could you ask for?”
