Cher appeared on David Letterman last night for an in-depth interview that touched base on the concerts she has been giving in Las Vegas for the past three years, her son Chaz Bono and his female-to-male gender transition, as well as her upcoming movie co-starring Christina Aguilera, Burlesque that opens Thanksgiving day.

The interview was a lot of fun to watch because Cher is just hilarious. She’s an entertainer, of course, but seeing her in an interview setting is especially great because she cracks jokes, she laughs at herself–and at David Letterman–and she doesn’t take herself too seriously. That quality alone interests me the most when it comes to celebrity interviews.

A good portion of the interview, while entertaining on Cher’s part and also a little more serious in part, was awkward to watch on David Letterman’s part. For one, it was uncomfortable to see just how confused David Letterman seemed to be about the whole concept of gender identity on the topic of Chaz, and how it does not designate a person’s sexual orientation. I kept wondering if perhaps he was trying to get the sometimes necessary clarification for his viewers who may not be as well versed as others on the topic, but after watching the clip multiple times, I still don’t know, and if there’s one person who should not seem overly awkward and make the viewer feel uncomfortable as they watch something, it’s the host.

Take a look at Cher’s interview with David Letterman below: