From Brass to Brushes: The Story of Hilton Head Painter Billy Howe

Billy Howe
Sep 16
3 min read

Updated: Oct 6

How a working musician found a steady rhythm in paint.

People ask me all the time: “Why is your business called Daygig Painting?”

It’s simple. For most of my life, the real job was at night.

I made my living with a trumpet — eight days a week, sometimes more! 😉

Weddings, conventions, clubs. Motown, disco, swing, whatever the night called for.

Music Was First

Brassfire, Plant City, FL — 1983. The horns were loud; my mullet was louder.

But before the gigs and the travel, it started simple — back in Indiana, with my dad’s old cornet in the attic. Once I found that horn, music was the course. By high school I was wrapped up in jazz band. By college I was gigging steady anywhere I could.

After graduation, I didn’t apply for an office job. I went straight to Kings Island outside Cincinnati, playing trumpet every day. That led to a downtown horn band, then touring the Midwest with a show group. Before long, I was in Florida with a house gig on Cocoa Beach — six nights a week, horn in hand, lights in my face. That was life.

Hilton Head and The Headliners

The Headliners on Kiawah Island back in 2000. Video quality has come a long way, hasn't it?

In 1985, Hilton Head called. I joined The Headliners, and we stuck together for 35 years. We played just about everything — weddings, corporate events, island parties. For twenty years straight we were voted the island’s best band. We made a lot of music and a lot of friends. Corporate gigs took us everywhere: Bermuda, Hawaii, New York, San Francisco. We even got flown into Barbuda for a surprise 40th birthday party. But most of it was closer to home — Boca, Naples, Marco Island, all over the Southeast. About 200 nights a year, year after year. Music was my career, plain and simple.

Finding the Day Gig

Still, music leaves daylight. You can’t rehearse all day. The slow seasons come. And when you finish a gig at one in the morning, the bills are still waiting.

That’s when I started painting. At first it was odd jobs — a rental house that needed work, a neighbor’s trim, a living room for a friend who trusted me not to spill on the carpet. I liked it right away. The prep, the clean lines, the way one sharp edge could change a whole room. Word spread, and one job turned into another. The day gig started to matter.

The Overlap

People laugh when I compare music and painting, but they’re not that different. In a horn section, one wrong note pulls everyone down. In painting, one sloppy edge ruins the wall. Both take precision. Both take stamina. Both mean showing up, even when you’re tired, and doing it right.

Music gave me endurance — long sets, steady time, blending with a section. Painting taught me patience — structure, prep, detail. They worked together.

Where It Landed

You can still sometimes find me playing live around the Lowcountry with Tower of Funk and the Choosy Mothers Horns.

What began as a way to fill daylight turned into a business. Daygig Painting grew into steady work. The name stuck because it was true: music at night, painting by day.

Now painting is the full-time job. Daygig Painting has proudly been serving the greater Hilton Head Island area since 2002.

But the horn never left. I still play, now with Tower of Funk and the Choosy Mothers Horns, keeping brass lines alive around the Lowcountry. My music calendar isn’t as wild as it once was, but the rhythm is the same: music at night, painting by day, and pride in both.

That’s the story. From brass to brushes.