How does the true fan of R. Kelly’s music balance the pleasure that music provides with the unpleasant knowledge of the acts he’s been accused of? Should the private actions of an artist ever impact the appreciation of the art? And what is the responsibility of the fan who supports an artist whose misdeeds are hurting others?

Jenny Benevento is a librarian, a blogger, a cultural commentator, and co-host of the pop-culture podcast “Jenny & Paul Sell Out.” Last October, she participated in an evening entitled “R. Kelly 101: Trapped in the Closet—What, How, Why?” sponsored by Homeroom at the Hungry Brain.

Jake Austen, who also sat on that panel, went to high school with Kelly at Kenwood Academy. He is the publisher of Roctober, the force behind the public access television show Chic-A-Go-Go, the singer in the Goblins, and the author of several books, including Flying Saucers Rock ’n’ Roll: Conversations with Unjustly Obscure Rock ’n’ Soul Eccentrics (Refiguring American Music) (Duke University Press) and Darkest America: Black Minstrelsy from Slavery to Hip-Hop (W.W. Norton).

Here are some of the highlights of the interview with Austen and Benevento:

(Austen references the Pitchfork Music Festival’s earlier booking of Odd Future several times during the chat; here is the long interview I did with Pitchfork’s top executives about that in 2011.)

Austen: The thing about him is that he’s shameless and he uses it to his advantage. A lot of his writing is about shamelessness, a lot of his excess is about shamelessness, and he doesn’t have any remorse

Benevento: Is the intentionality of this ‘this is a totally ironic act to bring to Pitchfork’? I think it’s a mix. I think that’s why he’s so successful. His music is so great, but hipsters can ironically enjoy these hilarious lyrical themes. The lyrical themes are alien to everyone’s life; no one can really identify with R. Kelly’s lyrics.

Austen: It seems like R. Kelly’s sex songs are just about him; they’re not about a partner. They all take place in his mind. There’s no other characters in these songs, really… It’s not real, and I absolutely understand why it’s hard to separate this fantasy thing from the actual sex that he’s had, but it’s hard to hear those songs and thing about human beings.

Austen: Of course you are right to ask them [Pitchfork] those questions, but the reason they’re right not to answer them is they don’t want R. Kelly to not do the show… It seems like Pitchfork the website would want to talk about this; that’s a good place to talk about it. But this festival thing is a separate thing in a way. Ideally, you are right. This is something that should be talked about. But you understand why they’re not going to. When a journalist is also a promoter, it puts them in a bad position.

Benevento: I think tourism is a great term for it. It’s like, “Oh, I’m just watching this freak show….” Just because I paid money and am totally supporting this financially it doesn’t mean that I really support this….

Benevento: I do think that bro, macho culture is there in indie rock just as much as it’s there in every other kind of aspect of rock n’ roll. It’s just maybe a little bit more underground. It’s not separate water fountains now, it’s just this casual racism. In the same way, I think there’s a lot of casual sexism, where it’s like, ‘Come on, it’s just fun to watch R. Kelly, why do you have to bring me down with this rape idea? It doesn’t matter ’cause it’s fun and it’s really good music.’

Ahead of R. Kelly headlining Pitchfork Music Festival, WBEZ’s Jim DeRogatis conducts a series of conversations with smart, passionate cultural critics. Videos have been edited for length and clarity.