Vermont’s Funniest Singer Doesn’t Mean to Write Comedy Songs. Seriously.

James Kochalka is by trade a cartoonist. This will surprise you not one iota once you hear his songs. Even reading the titles will give you the idea. “Miniature Stairway to Heaven.” “A Donut Named Maria.” “Queen Latifah’s Teeth.” “I’m So Woke.”

Like a great stand-up comic, on his new James Kochalka Superstar album How to Tie a Tie on the Internet, he hits the punchline and goes out on the laugh. Most of the songs run under two minutes. Some don’t even top one. The bulk of “Queen Latifah’s Teeth” is just him repeating the title line over and over. And here are the lyrics to “A Donut Named Maria,” in their entirety:

I’m in a love with a donut, a donut named Maria
But she’s in love with a hot dog named Oscar Gonorrhea
Oh don’t you know, the powdered sugar falls like snow
And I feel very cold and lonely without my donut

When asked how he comes up with his hilarious lyrics, he bristles. Or, whatever the friendliest form of bristling is. “I have no particular interest in writing funny songs at all,” he says. “I’m just writing songs that are me. I wish that critics realized that something being funny doesn’t make it less important or meaningful as a work of art. The silly man’s life has the same depth of meaning as the serious man’s life.”

He’s got a point. Like his massively popular comic strip American Elf, these songs’ humor comes not in the laugh-a-second jokes of Weird Al but more in the absurdist premises of, say, They Might Be Giants. Also, focusing solely on the lyrics does a disservice to his gift with an insanely catchy melody.

But…it’s hard not to focus on those lyrics. Take the new album’s title track. It’s exactly as advertised – but good luck following his tie-tying instructions. “I wrote ‘How to Tie a Tie a Tie on the Internet’ on the day that I was formally named the first Cartoonist Laureate of Vermont by the state legislature,” Kochalka says. “I probably hadn’t worn a tie since some event forced me to as a teenager. So, like everyone these days, I had to look it up on the internet. I actually couldn’t understand the directions, and invented my own way of tying a tie… which is similar, but somehow wrong.”

Many songs’ inspirations are equally straightforward – he wrote “Queen Latifah’s Teeth” because he liked saying “Queen Latifah’s teeth” – but not all. For instance, “Miniature Stairway to Heaven” is a power ballad about stairs intercut with a faux-rap verse parodying hip-hop braggadocio. But there’s more to the story.

“Miniature Stairway to Heaven is kind of about my brother in law getting a lung transplant this past year,” he says. “I actually began writing the song twenty years ago, but I only had one line. It took me twenty years to figure out how to expand it. It finally came together in 2017 when my brother-in-law was on a waiting list to get a transplant. His name [Kevin] rhymes with heaven. The day I recorded it is the day he got the transplant. He very nearly died, lost something ridiculous like 80% of his blood. Anyhow, I played the song for him after the operation, when he was quarantined to a hotel room near the hospital. It really felt like we were chillaxing in a tiny little heaven.” As he says, it’s not all just about the laughs.

“Miniature Stairway to Heaven” is, incidentally, not the album’s only track to reference Led Zeppelin. He recently listened one of their albums for the first time and felt like nearly every song referenced Tolkien. “I just imagined being that guy, reading The Hobbit, and then like running to write a song to express how it made him feel.” The result? “I Read the Hobbit.”

I could write about every song, but reading this post would take longer than listening to the full 22-minute album. So I’ll end with the rare topical song: “I’m So Woke,” which he wrote after joining Twitter. “The left end of Twitter is basically a constant battle of people trying to prove they’re more woke than anyone else,” he notes. “And if you can successfully call out a self-proclaimed woke person as being actually un-woke you win massive points.”

It’s a smart observation. It’s also – sorry James – pretty damn funny.

Buy James Kochalka Superstar’s full album ‘How to Tie a Tie on the Internet’ on Bandcamp.