Unlikely, that is, until you learn Wilson and the former Gov go back to 1963, when they were both first-graders in Mrs. Schlenker's class at Emmanuel Christian Day School.
"We were best friends," Wilson said. "We took different paths. I don't think either one of us understands the other's work."
Even so, there was no question who would paint Ehrlich's official state portrait, which will be unveiled June 3 at St. John's College.
Wilson said Ehrlich put it to him this way: " 'Billy' - he calls me Billy - 'you're going to paint my portrait.' "
The assignment was one of the toughest ever for the artist, who's created an album cover for Jacko (Blood on the Dance Floor) and painted a woman in an Army jacket for Penthouse (not as racy as it sounds, Wilson says).
"The better you know your subject, you go into subtleties that you wouldn't even be aware of," said Wilson, who is still putting on finishing touches.
"When I'm with the painting, do I feel like I'm in the presence of this person? And Bobby, it was difficult. ... It took me a long time before I captured what I was going after. ... Just being a local kid from Arbutus becoming governor. But at the same time, the presence and the power of the governor."
The portrait remains under wraps, but Wilson shared some details.
Ehrlich is shown in the governor's office, sitting on the corner of his desk, holding a book. He's wearing a suit. But in an informal touch, two plastic wristbands peek out from one sleeve. The orange one promotes disabilities awareness. The blue one honors Conner Hopf, an Ellicott City boy who died of Tay-Sachs disease.
Guess who'll be looking over her shoulder
Kendel Ehrlich's official portrait gets its official unveiling along with her husband's, but it's already on display on the artist's Web site.
The former first lady, decked out in a strapless green gown, stands on the curved Government House staircase. Behind her are pictures of the Ehrlichs' two sons, Josh and Drew.
Also visible is the corner of a larger portrait - the one Wilson painted of the former Gov. Annapolis artist Moe Hanson worked with Wilson to incorporate part of his painting into hers.
"She really wanted the family there," Hanson said. "I wanted her to be the main focus."
The paintings-within-the-painting were the happy compromise, if you can imagine such a thing in Annapolis.
There's always a kid brother
Mike Miller was chairman of that Senate committee way back when Zappa testified. Highlight of the future Senate president's career, if you ask Miller's kid brothers.
"My younger brothers, particularly one who is 13 years younger than myself, was a great Frank Zappa fan and was quite excited. He was just impressed that his big brother got to meet him and talk to him."