Archive for Bobby Conn

On Tyranny: Bobby Conn Doesn’t Mince Words About ‘Con Man’ Donald Trump

Posted in Features, Interviews, On Tyranny with tags , , , , on 09/05/2025 by Kurt Orzeck

“The goal of fascism is control and power. That’s the whole thing. That’s it. There’s no ideology beyond that. … Maybe we’ll make it through this. But I don’t know for sure.”
-Bobby Conn

Chicago’s own Bobby Conn is a king among troubadours, a musician’s musician, and yet also a musician who fights for the people, á la Billy Bragg. His last name is perfectly ironic, as Conn is best known for speaking truth to power and dutifully serving as a protest musician since he started playing music in 1989 with the avant-garde group Conducent. Five years later, that band broke up and Conn embarked upon his journey as a solo artist, which resulted in eight studio albums.

His ninth, Bobby’s Place, just arrived in late August. It’s pretty far out there, dubbed a “split-personality” record in which the first half tells a fantastical story about him living on an astral plane, while the second half imagines him as the star of an alternative-reality workplace sitcom named “Bobby’s Place.” The project captures and sustains the eccentric personality that Conn has embraced throughout his career, which has showcased him as a performance artist, glam-rock devotee and unabashedly outspoken critic of American politics and culture.

When The Bad Penny interviewed Conn via video before the release of Bobby’s Place, he noted that it is his least political record to date. That said, he told Splendid Magazine in 2008 that “All the records that I’ve done are a critique of what’s going on in contemporary America.” And with that in mind, Bobby’s Place can’t be considered detached from reality, even if some of the storylines he tells take place in an alternate reality.

That debate aside, we invited the highly politically opinionated legend to participate in our ongoing series On Tyranny, and he graciously and enthusiastically obliged.

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