Come on, My Immortal is most saddest, hauntingly and crying song. Most saddest song of all time. 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 -- … Although it might sound counter-intuitive, listening to sad music when we’re sad can actually help us … By. Listen to our Spotify playlist for the saddest songs of all time, and prepare for an onslaught of emotion. The second time I heard it my heart was entranced. Come wallow with us. 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. Sometimes the best cure for a broken heart is to listen to a ton of heartbreaking songs. Contrary to popular belief, not all sad songs are about a flunked love affair. Throughout the decades, hip-hop has produced plenty of songs about emotional darkness and depression. The 50 most depressing songs of all time - listen. All these emotions and stresses of life build up over time and at some point, we’re bound to reach our boiling point. ... keep my love as light as a feather. Jackie's Nella Fantasia is really so good but My Immortal is so very very sad. Sad songs to get you crying like a baby – let it all out with the 50 best tearjerker anthems by artists ranging from Leonard Cohen to Drake. 1. “Adagio for Strings,” Samuel Barber. Elton John, on listening to sad music, once said “It feels so good to hurt so bad”. 40 Saddest Country Songs of All Time Cry, Cry, Cry: From George Jones to Brad Paisley, the biggest weepers ever. Well, we couldn’t agree more. 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