Kanye West "Bad News" (2008)
Softest Lyric: "Oh you just gon' keep it like you never knew/While I'm waiting on a dream that'll never come true"
The best medicine for heartache is risky sexual behavior. With that said: Ever wanted to dabble in auto-erotic asphyxiation? "Bad News" is your soundtrack. Granted, we could have just picked all of 808s and Heartbreak, but what's special about "Bad News" is the timing of the song. Whether by design or unintentional genius, the two minutes of the song (the part where Kanye pain-croons) are the exact amount of time one would need to disrobe themselves, tie a belt around their neck, secure the other end in a door frame, fluff, and slowly begin to restrict blood flow to their brain.
Once oxygen levels drop, you are going to start feeling lightheaded from all the increased levels of carbon dioxide. This is normal. Do not panic. After Kanye says "channel cruise," you are going to start experiencing an increasingly intense feeling of eroticism. Congratulations. You now have one minute and 25 seconds to do your business. If you aren't done or near completion around the 3:15 mark, where the string's last reverbed note dissipates, then abort mission. You are in danger of dying. Don't try to be a hero. You don't want your parents finding you post-mortem and post-orgasm like that.
Remember, this is an amateur's guide to auto-erotic asphyxiation. With practice, you'll be able to last the entirety of "Pinocchio Story."