A disappointing episode that seems to have been made to give a guest star some time in the spotlight. Usually this show works because the four main characters can be paired up in different ways, usually allowing two story lines that don't even have to be connected. Here Karen is put together with guest star Madonna, and the three others get the second story line. A problem with the latter is that one character proves to be underused. Will's drug problem would be a good story for Will and Grace, or for Will and Jack. In the present form Jack is not used to his full potential.
An even bigger problem is the way Karen is portrayed. Her lack of knowledge about the real world is a running joke in the show, but there's also another side to her, as she is a no-nonsense, acerbic snob. The writers seem to have forgotten about the latter. I couldn't understand why Karen would even hang around with Liz. The curiosity was overdone, the wit underplayed. Karen became a stooge for the guest star. Sad.