Sad Country Songs 2019 25 Heartbreaking Country Songs From 2019 Guaranteed to Make You Ugly-Cry. Here's our list of the top 50 saddest dance music picks of all-time, from sad love songs to depressing songs about death. Throughout the decades, hip-hop has produced plenty of songs about emotional darkness and depression. The best sad songs will always make you cry. We write the saddest songs. We just really love sad songs. Warning: these songs might make you feel sad or angry; if that's the case, get in a good mood with the best dance songs of 2019. “sex money feelings die” by Lykke Li. The best part of breaking up is not the making up. While many consider it to be lazily written, I understand the true meaning of the words, and the emotions evoked in this song. Such a beautifully sad, heart-wrenching song. Looking for sad breakup songs? Sometimes the best cure for a broken heart is to listen to a ton of heartbreaking songs. What can I say?” Taylor Swift and Joe Alwyn in Oct. 2019 in New York City. Angel Olsen – “Windows” This is a sad song with a secretly positive message. 51 Sad Songs for When You Just Want to Sit with Your Feelings. To celebrate the end of the 2010s, Entertainment Weekly is looking back at the best pop culture of the decade that changed movies, TV, music, and … Check out the 73 best heartbreak songs, including hits from Kelly Clarkson, Miley Cyrus, Justin Bieber, and Taylor Swift. Here are our 50 favorite of the saddest songs: 50. From Taylor Swift and Bon Iver's "Exile" to Meek Mill and Roddy Ricch's "Letter to Nipsey," this is our running list of the best sad songs of 2020. If your favorite is missing, add it to the comments section below. Jul 26 2019, 2:14 pm EDT ... We’ve rounded up the best sad modern pop songs for when you’re feeling down, but still want a little sunshine. By Chelsea Peng, Ineye Komonibo and Bianca Rodriguez. 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