Come wallow with us. People write about war, depression, the loss of a loved one and ample of other things that you will find in this list. Like Led Zeppelin's 'All My Love' (see elsewhere on our list of the 25 Saddest Songs Ever), 'Tears in Heaven' is about the tragic death of a young family member -- … Listen to our Spotify playlist for the saddest songs of all time, and prepare for an onslaught of emotion. The 50 most depressing songs of all time - listen. Throughout the decades, hip-hop has produced plenty of songs about emotional darkness and depression. Well, we couldn’t agree more. The 100 saddest songs, according to Adam Brent Houghtaling, author of This Will End in Tears: The Miserabilist Guide to Music:. 40 Saddest Country Songs of All Time Cry, Cry, Cry: From George Jones to Brad Paisley, the biggest weepers ever. Sometimes the best cure for a broken heart is to listen to a ton of heartbreaking songs. Seriously—it's science! Come on, My Immortal is most saddest, hauntingly and crying song. Jackie's Nella Fantasia is really so good but My Immortal is so very very sad. Most saddest song of all time. Although it might sound counter-intuitive, listening to sad music when we’re sad can actually help us … The second time I heard it my heart was entranced. Elton John, on listening to sad music, once said “It feels so good to hurt so bad”. If you need to wallow in heartache, here’s our heavy dose of the saddest country music of all time.. No matter where we are in life, we’ve all lost someone or something at some point – it could be a lover to another, a job to the economy, our other half to divorce or death, a child who grows up and away, or even our innocence and youth. 1. “Adagio for Strings,” Samuel Barber. One study found that listening to sad music "can lead to beneficial emotional effects such as regulation of negative emotion and mood as well as consolation." 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