Practically all the time! It’s been that way ever since I was young.
When I was studying Othello, I found myself sympathising with Iago. I knew that what he was doing was wrong (manipulating Othello’s mind so that he believed his wife was having an affair). But for some reason, I could understand why he was angry at Othello. He had been Othello’s friends for years, and yet Othello favoured Michael Cassio over him. Having been in loads of trio friendships in the past, and knowing full-well that three is a crowd, I found myself identifying with him. But I knew that he was taking his bitterness a step too far!
I also feel sorry for Monsieur Verdoux. He is the central character of the story, so it’s hard not to find yourself liking him, if only just a little. Yes, he marries rich widows and murders them – but when you realise his backstory (his invalid wife and young son, and how he got laid off from work despite his hard work and loyalty) you do begin to see he is not really evil, just desperate to support his beloved family.
The one I feel most sorry for is Claude Frollo. He does really terrible things but he does them because he believes that they will please God. Everything he does, even killing Esmeralda, he does to try and redeem himself to God for lusting after a woman.