I thought that Mermorex commercial in the 70s showed Ella Fitzgerald's voice could do it even when recorded on tape.
And of course let's not forget La Castafiore...
I always wondered about that myself. Thanks for posting, R2, and asking, OP.
I think it would depend on the glass and the singer. Different glasses vibrate at different frequencies, probably depending on thickness (shape?).
This reminds of that old Get Smart episode, where Control engages the services of a big fat opera diva to crack glass with her voice. When she can't do it, she crushes it with her body instead.