The Boss covered "It's Over," but Orbison's "Crying" is not a song to be taken on by the faint-hearted. If hubris doesn't get you, the vocal range will.
I like k. d. lang's treatment of it, although her high-powered performances never really seemed to capture the wistfulness of it the way I'd like. For that, you have to go back to Don McLean:
And, of course, there's Rebekah del Rio's amazing cover at the club Silencio.