Meet Henry Hall, Your New Favorite Stand-Up Musician

“I want there to be a combination of humorous hopelessness to my music”

by Leora Yashari

They say the pressure to entertain can be hard—unbearable even.

In 2001, a fourth-grader named Henry Hall had inescapably succumbed to that pressure. Hall was plagued by a classic fourth-grade dilemma: His classmate would only share his Hot Cheetos under the condition that Hall perform his ever-popular Hot Cheetos bit. His hands were tied, really, and he had no choice but to comply. He grabbed a handful and swallowed them whole. He waved his hands around his ears, pretending smoke was coming out, screamed for water, and flailed about the classroom as his friends cheered.

“I’ve been doing a version of that Hot Cheetos bit my whole life,” he says.

The pressure to entertain for Hall was innate, or more literally, it was inherited. He’s the son of small-town, little-known comedians Julia Louis-Dreyfus and Brad Hall. He’s also a graduate of the Crossroads School of Arts and Sciences, the illustrious K-12 playground for the entertainment elite and their progeny. (As a fellow graduate, we live to poke fun at our alma mater.) 

But for Hall, being an entertainer was only part of a much larger dream. He spent his formative years training in classical music. A self-proclaimed band geek, his classroom bits extended to indie-rock band gigs from middle school through his college years. 

Now, the 25-year-old is shaping his own music career—he’s released three EPs and a new single called “Love for Serious” already as a solo artist and is preparing to put together a full-fledged album in the coming year. 

“I always found music to be the most direct form of expressing the human experience,” he says. “You’re creating these sounds that just kind of float in the air, and they’re inherently indescribable—you can’t really put your finger on it—it’s like describing a color or something.”

On any other subject, he can barely get through a sentence without a sarcastic quip, a joke that will force even the saltiest person to laugh out loud. And yet, music seems to be his grounding point. From an early age, he was inspired by the music introduced to him by his parents. 

“My dad is a massive Beatles fans. One of few Beatles fans—one of the maybe nine Beatles fans,” he jokes. “He exposed me to a lot of the music I still know and love today, like Simon and Garfunkel, The Smiths, Joy Division…”

After years of performing for audiences, ranging from fraternities to one very pissed-off Pittsburgh native in a small New York bar, his career as a musical artist began shaping itself. With his ethereal high-pitched vocals, his sound lies somewhere between Best Coast and Morrissey, maintaining a comically discerning “sad guy” image. Hall’s self-described “weirdo” quality of music comes across as something new and authentic.

“I want there to be a combination of humorous hopelessness to my music,” he says. “I want to weird people out as much as I can and hopefully, make them laugh or make them look at me very strangely. Eliciting any reaction is good.”

In many ways, Hall’s budding career is a manifestation of a new form of entertainer. His sets are a mixed bag of raw, vulnerable lyrics and unabashed stand-up comedy. That’s often the way he engages a crowd—by making a joke or telling a lurid story that grabs attention before singing about falling in love with his ex-girlfriend’s sister

And, his aspirations to continue classroom laughs are trailing right behind his music career. He’s teamed up with two of his fellow Wesleyan University classmates and filmmakers, Jack Coyne and Jack Pearce (or Jack Squared, as he refers to them) to launch a series of video shorts called “What’s Up YouTube?” The described premise is a candid look into the unglamorous reality behind a vivacious YouTube vlogger. Hall plays the principal character, bringing all the dark humor of Andy Samberg’s SNL digital shorts combined with the loud irony of Eric André. 

“It’s sort of like a short film version of what I’m trying to go for in my music,” he says. “I’m finding a way to synthesize the two.”

As Hall prepares for upcoming shows in Chicago and New York, he hopes his career is heading to a point of writing, touring, and making people laugh on a day-to-day basis. Though he never tries to emulate any other comedian, he does have his favorites: Norm MacDonald, Rodney Dangerfield, Dave Chappelle—and his mom, of course. When asked what his ultimate dream for himself is, he does not hold back: “Probably to be like the quarterback of the Dallas Cowboys,” he says, waiting at least seven seconds before breaking into laughter. “I love to play music and perform, other than being on the football field and smelling that green grass, of course.”

You can watch the premiere episode of Henry Hall’s YouTube short, below.