The 100 saddest songs, according to Adam Brent Houghtaling, author of This Will End in Tears: The Miserabilist Guide to Music:. ... keep my love as light as a feather. 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 -- ⦠The first time I heard it my senses were shocked. Well, we couldnât agree more. Sad songs to get you crying like a baby â let it all out with the 50 best tearjerker anthems by artists ranging from Leonard Cohen to Drake. If you need to wallow in heartache, hereâs our heavy dose of the saddest country music of all time.. No matter where we are in life, weâve all lost someone or something at some point â 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. By. Sometimes the best cure for a broken heart is to listen to a ton of heartbreaking songs. 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." Come on, My Immortal is most saddest, hauntingly and crying song. Contrary to popular belief, not all sad songs are about a flunked love affair. 40 Saddest Country Songs of All Time Cry, Cry, Cry: From George Jones to Brad Paisley, the biggest weepers ever. Come wallow with us. The second time I heard it my heart was entranced. 1. âAdagio for Strings,â Samuel Barber. For some reason, we gravitate towards listening to sad songs when weâre feeling blue. Although it might sound counter-intuitive, listening to sad music when weâre sad can actually help us ⦠The 50 most depressing songs of all time - listen. People write about war, depression, the loss of a loved one and ample of other things that you will find in this list. Jackie's Nella Fantasia is really so good but My Immortal is so very very sad. 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