Do not presume a lack of agency that Willis, by most accounts, indeed possessed. Winterbottom, a Chicago-based artist who roomed with Willis for roughly seven years during the ‘90s, describes a man who couldn’t cook or tie his shoelaces, but was also an extraordinarily self-driven artist with a shrewd sense of promotion.
“He was savvy enough to realize what sold. If he wrote you a love song, you were gonna buy a few copies,” says Winterbottom. “And the same with the band tributes. He was a very smart marketer. In a sense, Wesley exploited his audience as much as anyone could’ve exploited him.”
Winterbottom’s take on the music itself is instructive, too, finding more craft and intentionality than might appear at first blush. “He took it very seriously. He’d pick around on the keyboard. He was very specific about finding the right key and tempo. He’d work it out musically. Wesley crafted his music according to his own style -- it’s kind of charming and childlike but also introspective and uplifting.”