Wild World by Cat Stevens. "Now that I've lost everything to you; you say you wanna start something new and it's breakin' my heart you're leavin'" Seems to be about a breakup but he states it is about his return to music after almost dying. Either way sad. #musicsky #nowplaying youtu.be/Jta56wBl7SM

Cavalier by James Vincent McMorrow. Really great SSOTD. "Speak until the dust settles in the same specific place, light refused to go." Poetic, nostalgic, deep, and beautiful song. I remember my first love! #musicsky #nowplaying #music youtu.be/j0DvjgagJko?...

Boots of Spanish Leather by Bob Dylan. A tale of two different sides of love. "Sayin', "I don't know when I'll be comin' back again It depends on how I'm a-feelin'" One of the saddest lines ever. One only wants love but the other is out wandering. #musicsky #nowplaying #Dylan youtu.be/iy6wryJMwVU

In celebration of 10,000 followers, here are my top five SSOTD's. 1. Daughter by Youth 2. Charon by Keaton Henson 3. Gasoline by Houndmouth 4. Fond Farewell by Elliot Smith 5. This Night Has Opened My Eyes by The Smiths Please share your top 5! #musicsky #nowplaying #music

10am Gare du Nord by Keaton Henson. Very sad! "Please do not hurt me, love, I am a fragile one and you are the light in my eyes. Please do not break my heart I think it's had enough pain to last the rest of my life." Obsessive love-about his breakup. #musicsky #nowplaying youtu.be/8LluhRTBk9g?...

Baby Britain by Elliot Smith (Seth Avett & Jessica Lee Mayfield). Heartbreaker! "Separated from the rest. Fights problems with bigger problems." About a friend who is struggling with addiction and falling apart. Elliot Smith classic, catchy and sad. #musicsky #nowplaying youtu.be/gimnxa4AltE

Empty As a Drum by Turnpike Troubadours. Sad storytelling. "But here's to hopin' she'll still come. I'm too old to be this dumb." Written like a short story. Empty without her and filling it with drinking. She showed up but oh what a mess they got into. #musicsky #nowplaying youtu.be/rsIanTh3G0E

Helpless by Crosby, Stills, Nash & Young. This one sticks in my head. "Babe, can you hear me now? The chains are locked and tied across the door. Baby, sing with me somehow." Neil Young's childhood; about polio, divorce, and longing. #musicsky #nowplaying #CSNY youtu.be/G7CHSv8c77w?...

500 miles by Hedy West covered by Joan Baez. This is really a classic SSOTD, goes way back in folk music. "Not a shirt on my back, not a penny to my name. Lord I can't go on this a-way." Traveling, too poor to go home but homesick. Great version. #musicsky #nowplaying youtu.be/B_K6z3HiRAs

Blues Runs the Game by Jackson C. Frank covered (Laura Marling). Tragic song and life. "Maybe tomorrow, honey, someplace down the line. 'll wake up older So much older, mama. I'll wake up older and I'll just stop all my tryin'". Mental illness and tragedy. #musicsky #nowplaying youtu.be/ZpDsPb9aZFs

The Funeral by Band of Horses. Great SSOTD and live version! "To the outside, the dead leaves they own the lawn; 'Fore they died and had trees to hang there upon." Written about his aversion to forced togetherness and mortality. Coming up only! #musicsky #nowplaying youtu.be/N_Xz6Aq5lwk

Charlene by Anthony Hamilton. One of my favorites! "Woke up this morning found a letter that she wrote. She said she's tired that I'm always on the road." Overall, it is his fault for putting music over her, but she should come back. #musicsky #nowplaying #Charlene youtu.be/QUmxh7H8vok

Using Again by Tod Benjamin. Hard hitting SSOTD. "The cost of my living was more than I planned so I held a needle like a gun in my hand." About his struggle with addiction. He no longer plays this song since he got clean. #musicsky #nowplaying #music youtu.be/NACMpkxm-fA

Crosses by Jose Gonzalez. Love this SSOTD. "People staring. They know you've been broken. Repeatedly reminded. By the looks on their faces." The song is about comforting someone who is struggling but also about his own struggle with mental illness. #musicsky #nowplaying youtu.be/4nC8WjPFnGU

See You Later, I'm Gone by Robert Lester Folsom. Chil Monday SSOTD. "Your summer smile has left me sad and though it's here it's not for me." Written when he was a college freshman about drifting apart from his girlfriend. Nostagic,sad and rediscovered . #musicsky #nowplaying youtu.be/_AGNRUR9xmg

Someday (Triple J LIke A Version) by the Stokes covered by Julia Jacklin. This is a sad banger! "Oh, my ex says I'm lacking in depth but I will try my best." Basically, relationships and life are hard but "I ain't wasting no more time." #musicsky #nowplaying youtu.be/Hl9FV9thfRE

Morning Song by the Avett Brothers. Good SSOTD. "Hurts so bad. You don't come around here anymore. Worse than that. Nothing really helping I've been thinking 'bout drinking again." Broken relationships and finding strength. #musicksky #nowplaying #Avett youtu.be/fBQZnHv74dQ

Vanilla (stairwell version) by Holly Humberstone. This SSOTD resonates with me. "And I could go on and on and on and on and on but the truth is: I have my best nights without you." recorded in a stairwell in her childhood home. Bottom line don't settle. #musicsky #nowplaying youtu.be/x8YhFtdeAiM

The SSOTD is Diamond and Rust by Joan Baez. Heartbreak. "Well, I'll be damned here comes your ghost again but that's not unusual." About an unexpected phone call from Bob Dylan. The memories are diamonds but tarnished with rust of pain and time. #musicsky #nowplaying youtu.be/IrVD0bP_ybg

Pitseleh by the late great Elliot Smith covered by Seth Avett & Jessica Lea Mayfield. This is a version you should check out! "I'm not half what I wish I was, i'm so angry." Pitseleh is a yiddish term of endearment (little one). About love and addiction. #musicsky #nowplaying youtu.be/GNnwasdCUPg

Stop Your Tears by Aldous Harding. A monster of a sad song. The first lyrics "I will never marry my love. I will die waiting for the bells. Death, come pull me underwater. I have nothing left to fear from hell." I mean, really! About all things. #musicsky #nowplaying youtu.be/naNmJ-ft4Ig

One More Try by George Michael. Classic sad song. "I'm so cold inside. I'm just not willing to try." He wrote it about leaving a bad relationship and being scared to enter a new one. At the end he decides "I said maybe just one more try." #musicsky #nowplaying youtu.be/bG5N3GC-m20

I've Got Dreams to Remember by Otis Redding. An Otis heartbreaker. "These eyes of mine, they don't fool me. Why did he hold you so tenderly?" One of the great voices of all time. Died to soon (at 26). Broken hearted music #musicsky #nowplaying #Otis youtu.be/hoLgUNj105E

Get You the Moon (Kina ft. Snow). Sweet but sad. "'Cause you are, you are the reason why I'm still Hangin' on. 'Cause you are, you are the reason why my head is still 'Bove water." About having a person in your life who keeps you going. Great colab! #musicsky #nowplaying #lofi youtu.be/eRnIks59Pjw

Safe Travels, (Don't Die) by Lisa Hannigan. To all the wonderful and kind people on Bluesky, this is my message for the weekend! "Like you always say, safe travels, don't die, don't die, safe travels, don't die. #musicsky #nowplaying #music #Hannigan youtu.be/X1k5ZlGMqto

Gasoline by Houndsmouth. One of the best sad songs! "It was only just then that I could see I was alone in feeling so lonely." Deep song about someone who can't connect and is self-destructive. Poor boy, cause when the morning comes she will be gone! #musicsky #nowplaying youtu.be/JBw6RSEFVU0

Stay covered by Cat Power. This is a great cover. "When you finally see the light. It's hard to know which one of us is caving." Cat Power decided to do this cover in reaction to an ex-lover. Cat Power is amazing!. #musicsky #nowplaying youtu.be/f-Tsk-cPXxI

Little Bird by Lisa Hannigan. I lost this song and I am so happy to find it! Lyrics-so good! "Your heart sings like a kettle and your words, they boil away like steam and a lie burns long while the truth bites quick. A heart is built for both it seems." #musicsky #nowplaying youtu.be/GRdj8MRj9Js?...

Nothing Else Matters by Metallica covered by Phoebe Bridgers. Amazing song and cover. "Never cared for what they do Never cared for what they know." Written on the road missing his family. About love, longing and values. A great song and cover. #musicsky #nowplaying youtu.be/tBjTZkl3qNU?...

Au Pays du Cocaine by Geese. Check this one out! "You can stay with me. You can stay with me and just pretend I’m not there." Title is In the Land of Cocaine or In the Land of Plenty. About having a partner who outgrows you. A desperate song. #musicsky #nowplaying youtu.be/RGE-JRsJ2uo?...

The Predatory Wasp of the Palisades is Out to Get Us! by Sufjan Stevens. Magical/sad "I can't explain the state that I'm in. The state of my heart, he was my best friend." Complicated song about sexual and spiritual awakening (and camp). #musicsky #nowplaying #sufjanstevens youtu.be/8DCav8NvbQQ?...

I'd Have to Think About It by Leith Ross. Sad on multiple levels. "And honest, I can tell you now I love you more than my future spousе." I think everyone has felt a love so deep you think you will never get over it. This is that put to a beautiful song. #musicsky #nowplaying youtu.be/yg8Vl6LfrKs

Dog Days Are Over by Florence + Machine. An bittersweet anthem. "And I never wanted anything from you except everything you had." Basically about chasing happiness, you better run! Maybe the dog days are over? Anyway, this is great live! #musicsky #nowplaying #likeatrain youtu.be/yNaLz-UTZ3w?...

Redemption Song by Bob Marley. More than a song. "How long will they kill our prophets, while we stand aside and look?" This song urges mental and spiritual liberation from oppression. He wrote it when he was dying of cancer as a message of freedom. #musicsky #nowplaying youtu.be/9ZpxaeICYyg?...

Never Had No One Ever by The Smiths. Sorry for this pre-valentine's day selection but..."And I know alone that I never, ever oh had no one ever." Alienation and isolation. Sad song about being an outsider. Here is to everyone finding belonging! #musicsky #nowplaying #smiths youtu.be/lYjedww3fNo

Jealous Guy by John Lennon and the Plastic Ono Band. I feel this song. "I was feelin' insecure you might not love me anymore. I was shivering inside." The best description of jealousy ever. He wrote it about his all consuming love for yoko. #musicsky #nowplaying #lennon youtu.be/wADRRYNHhOA

I'm Not Yours by the great Angus & Julie Stone. Beautiful, sad and powerful. "Light me up a cigarette and put it in my mouth You're the only one that wants me to die." Australian brother and sister band. About the disillusionment of an intense relationship. #musicsky #nowplaying youtu.be/Uj1AOKUPYTY

Boston by Augstana. Love this SSOTD. "You don't know me, and you don't even care, Oh-yeah, and you said." Basically, about leaving behind a broken relationship and starting over. "I think I'll go to Boston, I think I'll start a new life." #musicsky #nowplaying #Boston youtu.be/4ASJBXu8tNo

Is There Something in the Movies by Samia. Good and sad. "I only write songs about things that I'm scared of, so here, now you're deathless in art." Samia said it is about betrayal by someone honoring fantasy over her love. Also, about dying young. #musicsky #nowplaying youtu.be/yDWugAM82u8

Like The Weather by 10,000 Maniacs. I heard this at a coffee shop today and it took me right back. "For it's such a long time since my better days. I say my prayers nightly, this will pass away." About feeling down and staying in bed on a cold a rainy day. #mylife #musicsky youtu.be/RTzd2z4af30

Don't Let Me Be Misunderstood by Nina Simone. Deep song by a great singer. "I never mean to take it out on you. Life has its problems, and I get more than my share." Written based on a songwriters fight with his wife. Fitting as Nina had bipolar disorder #musicsky #nowplaying youtu.be/9ckv6-yhnIY

Baker Street by Gerry Rafferty. Really sad SSOTD. "Winding your way down on Baker Street. Light in your head and dead on your feet. Well, another crazy day, you'll drink the night away." About addiction, failure and life in london. #musicsky #Nowplaying youtu.be/Fo6aKnRnBxM

Bridge Over Troubled Water by Simon and Garfunkel. Classic SSOTD. "When you're weary, feeling small. When tears are in your eyes, I will dry them all. I'm on your side.'" Written to Simon's wife. Overall, I will lay me down! #musicsky #Nowplaying youtu.be/OKsXd_E6bDA

Far Behind by Candlebox. A good friday SSOTD. Now maybe I didn't mean to treat you bad, but I did it anyway." Written as a tribute to late singer Andy Wood who died of a heroin overdose. About mistakes, regret and loss.. #musicsky #nowplaying #90's youtu.be/eu3EuWg2qNI

Letter to Hermione by David Bowie. Really sad Bowie Song. "I care for no one else but you. I tear my soul to cease the pain. I think maybe you feel the same. What can we do?" A literal letter he wrote after Hermione Farthingale broke up with him. #musicsky #nowplaying youtu.be/Xw1mmqMD9j0

Touch by Sleeping at Last. Listen to the SSOTD! Like a poem. "Pain is a well-intentioned weatherman predicting God as best he can. But God, I wanna feel again." Too much! About numbness, emotional detachment, and wanting connection. Great band and song. #musicsky #nowplaying youtu.be/ZtgxwkIhH5M

I Know by Fiona Apple. Great song and amazing artist. "And you can use my skin. To bury secrets in." and "I will ask no questions. While I do my thing in the background." About being in a relationship with someone who is committed. Heartbreaker #musicsky #nowplaying #Iknow youtu.be/wB09p4MF7gw

Black by Pearl Jam. One of the Classic SSOTD for a cold Friday. Devastating lyrics. "Now my bitter hands cradle broken glass of what was everything." About lost love. "all five horizons revolved around her soul." I mean really! #musicsky #nowplaying #pearljam youtu.be/qgaRVvAKoqQ

Without Me by Halsey. I always liked Halsey, this is a good angry SSOTD. "Put you right back on your feet, just so you could take advantage of me." Rumored to be about an ex-boyfriend. Ultimately, about building someone up only to be betrayed. #musicsky #nowplaying #Halsey youtu.be/ZAfAud_M_mg

I Can't Make you Love Me covered by Bon Ivor. Bonnie Raitt also has a great cover. "Just hold me close and don't patronize." It doesn't get any more powerful than those lyrics. Just give me until morning to do what's right and give up this fight. #musicsky #nowplaying youtu.be/Q3VjaCy5gck