Last year I had an article in the New York Timesโ€”a
personality piece about my then-dude that I wrote for their “Modern
Love” column. While it was somewhat shocking to see my (real) name in
that most-hallowed paper, it was more disconcerting to see the
illustration that accompanied it: a watercolor portraying an eerie
likeness of me and an eerier likeness of my dude. How did the
illustrator guess what we looked like? Was he stalking us? My curiosity
piqued, I asked my editor at the Times about it, and he directed
me to David Chelsea, who happens to live in Portland. David’s been a
working artist for 28 years. He got his start in high school,
illustrating for the Portland Scribe, a precursor to the
Willamette Week. He went to art school in New York and lived
there until 1995, when he and his wife moved back to Portland for more
elbowroom and to start a family. These days, David affords his swanky
Irvington lifestyle with two regular gigs: He’s done the calendar for
the New York Observer every single week since 1995, and has
illustrated “Modern Love” since 2004. Like many illustrators, Chelsea’s
true passion is comics, and his early-’90s graphic novel, David
Chelsea in Love,
was reprinted in French last year.

How much time does it take to illustrate one “Modern Love”
column?

It’s a solid two days out of my week. I get the manuscript on Friday
and send in six thumbnails by Monday. They get the finish by Thursday
and it runs on Sunday.

The piece you did for my column was creepy in its verisimilitude. Do
you Google people?

I did Google you, but the photos weren’t very useful as the piece
called for you to be clothed and seen from behind.

Any columns that have been particularly challenging? It’s
challenging coming up with new ideas because a lot of the same topics
keep coming up. I don’t like to recycle, but there’s only so many
changes you can bring to “birth mother finds long-lost kid.”

Was there a column that was particularly fun?

A couple of weeks ago I illustrated one that involved a woman who’d
just been divorced, and she volunteered for Katrina recovery, and the
magnitude of the suffering there sort of put hers in perspective.

What was the illustration?

I drew her standing in the midst of a house that’s collapsed on her,
but she’s been saved because there’s a heart-shaped window in the
attic. That was a chance to recycle a classic bit from a Buster Keaton
movie.

What’s the “Modern Love” piece you’re working on now?

It’s another birth-mother-finds-kid-after-13-years story.