The saddest song I can think of is Patty Loveless' "How Can I Help You to Say Goodbye?". It is a country song my mom used to listen to when we went to visit my uncle and aunt in Idaho. Really sad song. It's about a woman going to her mother whenever she loses someone-- I think the first two are a childhood friend who moves away and her husband via divorce. The last person the narrator loses is her mom. Seriously sad stuff.
Anyway, I haven't heard it in a long time because I heard it once when I was younger and sobbed. That was back when I had really bad asthma, so I got to having an asthma attack. After that, my mom didn't play the song anymore. My lungs were a real problem back then, and I bet my mom felt terrible.
I'm just happy, though, that I never had to hear that damn song again. It is seriously depressing. I get sad just thinking about it.
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