Oh yeah, Gordon has made me get teary-eyed a few times. Here are a few that get me all choked up.
If You Could Read My Mind: I don't think any song expresses the pain, confusion and heartache of a divorce/breakup any better than this.
Miguel: Not only is the story very poignant but the melody is haunting and tugs at your emotions.
Talking in Your Sleep: The lyrics say it all in this one. Is there anything more sad and depressing than lying next to your sleeping beloved while listening to them talk about there secret love? Me thinks not...
Go My Way: this may not be a "sad song" per se but there is a sweet sort of longing in the words and something about that line "Why must I sail my ship alone without a friend??" that gets me each time.