Had a minor windfall in the shape of the work World Cup sweepstake, so decided to buy earrings. In one of the shops I wandered around, I had my headphones on. The woman in the store asked me what I was listening to. When I said Ani Difranco she said "ah, old school." I smiled and nodded and carried on.
Ani Difranco put out a studio album in 2008 (Red Letter Year) and has since released a couple of live albums. So I'm not sure her school is too old. That said, I'd also say that her older work is more well-known and better liked. I'm in the old-school-Ani camp :)