Almost put Sam smith not in that way at no. 1

As a self-proclaimed chronic sad song listener, I live for those tracks that just get you. I’ve spent countless hours curating what I truly believe is the ultimate Top 10 playlist for when you need a good cry, a moment of reflection, or just to feel seen. Forget the generic lists; these are my deeply personal picks that have soundtracked countless introspective moments. Let's dive in, starting from number ten and building up to my absolute top tear-jerker! #10: Buddy's Rendezvous - Lana Del Rey & Father John Misty Kicking off the list with an underrated gem. Honestly, I could have included Lana Del Rey’s entire discography on this list, but this collaboration with Father John Misty is something special. The melancholic duet perfectly captures that feeling of bittersweet nostalgia and longing. It’s a beautifully understated track that you might miss if you’re not actively looking, but once it hits, it truly resonates with its quiet despair. #9: Love of My Life - Queen Beautiful. Sad. Need I say more? This song is an absolute classic for a reason. Freddie Mercury’s raw emotion, combined with the poignant lyrics, makes it an enduring anthem of lost love and enduring affection. Every time I hear it, it just hits me right in the feels. It's a testament to how universally understood heartbreak can be. #8: I Know - Fiona Apple Fiona Apple will never fail me, and the chorus of this song is just so good. Her ability to convey complex emotions with such raw honesty is unparalleled. "I Know" is a masterclass in vulnerability, weaving together feelings of insecurity, desire, and defiant self-awareness. It's a song that makes you nod along, thinking, "Yes, I know exactly what she means." #7: This House - Japanese Breakfast The build-up of this song is insane, and the lyrics are beautiful. Michelle Zauner has a way of crafting intimate narratives that feel universal. "This House" explores themes of memory, home, and the echoes of past relationships within familiar spaces. The way the song gradually swells, mirroring the intensity of lingering emotions, is simply breathtaking. It’s perfect for a rainy day. #6: Please Be Mine - Molly Burch Holy. F*ing. Yearning. That's the only way to describe this track. Molly Burch’s distinctive vocal delivery perfectly encapsulates the desperate plea for connection and validation. It’s a song about wanting someone so badly, about the vulnerability of putting your heart out there and hoping it’s met with the same intensity. It's a quiet, aching masterpiece. #5: Rodeo Clown - Dijon “I STILL WEAR THE T SHIRT THAT YOU GAVE MEEEEEEEEE.” This line just rips through me every time. Dijon has a unique way of capturing the messy, unpolished reality of love and loss. "Rodeo Clown" feels like a raw, unfiltered confession, a desperate attempt to cling to the remnants of a past relationship. It's intensely relatable for anyone who's ever struggled to let go. #4: j's lullaby (darlin' i'd wait for) - Delaney Bailey I've cried to this probably 400 times, no exaggeration. Delaney Bailey's voice, combined with the gentle, heartbreaking lyrics, creates an incredibly intimate and soothing yet profoundly sad experience. It's the kind of song that feels like a warm, melancholic hug, perfect for those moments when you just need to fully embrace your sadness. #3: Drew Barrymore - SZA But have you actually listened to these lyrics???? "AM I WARM ENOUGH FOR YOU." SZA is a poet of modern heartbreak and self-doubt. "Drew Barrymore" is a complex exploration of insecurity, seeking validation, and the fear of not being enough in a relationship. Her candidness makes every line sting with authenticity. It’s a masterpiece for anyone navigating the tricky waters of modern romance. #2: Thinking of You (Live) - Katy Perry SORRY NOT SORRY. Her magnum opus. You haven't lived until you've heard the live version. While the studio version is good, the live acoustic renditions of "Thinking of You" elevate it to an entirely different level of emotional raw power. It’s a song about a love that lingers, about memories that refuse to fade, and Katy’s live vocals convey that aching vulnerability with breathtaking sincerity. If you haven't experienced it, do yourself a favor and find a live performance – it’s transformative. #1: Not In That Way - Sam Smith** And finally, my undisputed number one. This song is the epitome of beautiful, understated heartbreak. Sam Smith’s "Not In That Way" captures the gut-wrenching pain of unrequited love, of being loved by someone who just can’t reciprocate your romantic feelings. The raw vulnerability in his vocals, the simple yet devastating lyrics, and the sparse arrangement create an overwhelming sense of poignant sadness. What makes this song particularly powerful, and why so many people search for a "Sam Smith Not In That Way cover," is its universal theme. The emotion is so pure and relatable that other artists are drawn to reinterpret it, trying to capture that same aching vulnerability. But for me, the original is untouchable. It’s a masterclass in conveying profound sadness with dignity and grace, and it consistently brings me to tears, no matter how many times I hear it. So there you have it – my ultimate playlist for those days when only a sad song will do. What are your go-to sad songs? I’m always looking to expand my collection!