The 10 Saddest Taylor Swift Songs That Will Make You Cry

Taylor Swift has a remarkable ability to craft songs that resonate deeply with our emotions, often bringing tears to our eyes. Her storytelling prowess and lyrical vulnerability create powerful connections with listeners, making her discography a treasure trove of poignant tracks. While many of Taylor’s songs possess the potential to evoke sadness, this list focuses on the top 10 Taylor Swift songs that are exceptionally heartbreaking, the ones that can reliably trigger a good cry. Let’s explore these emotionally charged masterpieces and see if your own list aligns.

10. Fifteen

“I found time can heal most anything, and you just might find who you’re supposed to be.” Taylor Swift’s songs often serve as soundtracks to different life stages, and “Fifteen” perfectly encapsulates the bittersweet nostalgia of adolescence. This track resonates because it taps into universal experiences of youthful naivety, first loves, and the inevitable heartbreaks that accompany growing up. Listening to “Fifteen” can evoke tears not just from the memory of past hurts, but from the poignant realization of personal growth and resilience. It’s a reminder of how far you’ve come and the journey you’ve navigated to reach your present self. The simple melody and honest lyrics make it a quietly devastating reflection on time and transformation.

9. All Too Well

“I’d like to be my old self again, but I’m still tryin’ to find it.” Whether you prefer the original or the extended 10-minute version, “All Too Well” remains a quintessential sad Taylor Swift song and a fan favorite for good reason. Its lyrical genius lies in its immersive storytelling. Taylor paints such vivid imagery and relatable emotions of a past relationship that listeners effortlessly step into the narrative. The raw vulnerability and detailed memories woven throughout the song create an intensely personal experience for the listener. If you’ve ever experienced a love that burned brightly and ended in heartbreak, “All Too Well” will undoubtedly trigger a wave of emotions and likely, tears. The sheer specificity and evocative language make it universally heartbreaking.

8. Tolerate It

“Gain the weight of you then lose it, believe me I could do it.” Taylor Swift’s mastery of breakup songs is undeniable, and “tolerate it” delves into the quiet agony of a relationship fading away. This song captures the feeling of being trapped in a love where you’re giving your all, but receiving minimal reciprocation. It portrays the painful realization that the person you love has changed, yet you still cling to the remnants of what once was. “tolerate it” explores the internal conflict of wanting to leave but being held back by lingering affection and the daunting task of confronting a painful truth. The bridge, in particular, with its desperate plea for recognition, is a guaranteed tear-jerker for anyone who has felt unseen and underappreciated in a relationship.

7. Never Grow Up

“It’s so much colder than I thought it would be, so I tuck myself in and turn my night light on.” Despite the absence of a Taylor’s Version for now, “Never Grow Up” remains a deeply relatable and profoundly sad song in Taylor’s discography. Alongside “Fifteen,” it speaks to the universal experience of confronting adulthood and longing for the innocence of childhood. The song encapsulates the fear and uncertainty that come with facing “grown-up” responsibilities and navigating the world independently. It’s a poignant expression of wanting to recapture the carefree days of childhood, free from stress and burdens. For anyone feeling overwhelmed by the pressures of adulthood or simply missing simpler times, “Never Grow Up” is an emotional trigger that can easily lead to tears of nostalgia and longing.

6. Marjorie

“I should’ve asked you questions, I should’ve asked you how to be.” Losing a grandparent is a profound life event, and “Marjorie,” written for Taylor’s grandmother, beautifully captures the complex emotions of grief and remembrance. The song resonates deeply with anyone who has experienced the loss of a close loved one. It’s a bittersweet reflection on cherished memories interwoven with the painful realization of missed opportunities and unspoken words. “Marjorie” explores the “what ifs” of grief, the things we wish we had said or done. The emotional weight of the bridge is intensified by the inclusion of Marjorie’s opera vocals in the outro, creating a haunting and deeply moving tribute that is incredibly difficult to listen to without tearing up.

5. Bigger Than The Whole Sky

“I’m never gonna meet what could’ve been, would’ve been, what should’ve been you.” “Bigger Than The Whole Sky” is a masterclass in lyrical ambiguity, allowing for multiple interpretations and deeply personal connections. While some fans interpret it as a song about miscarriage or infant loss, others see it as a broader reflection on any significant loss or absence in life. This very ambiguity is what makes it so universally heartbreaking. The song’s power lies in its ability to mirror individual experiences of grief and unfulfilled potential. Taylor’s delicate vocals and the ethereal instrumentation amplify the song’s emotional impact, creating an atmosphere of profound sadness and quiet devastation that can easily bring listeners to tears, regardless of their specific interpretation.

4. Would’ve, Could’ve, Should’ve

“God rest my soul, I miss who I used to be.” Similar to “All Too Well” in its fan adoration and emotional intensity, “Would’ve, Could’ve, Should’ve” from the Midnights album is a raw and unflinching exploration of trauma and lost innocence. While it may not achieve mainstream single status, Swifties recognize its power as one of the Saddest Taylor Swift Songs. It delves into the long-lasting impact of a damaging relationship that fundamentally alters one’s sense of self. The song speaks to the lingering scars of being taken advantage of by someone trusted and the subsequent struggle to reclaim a sense of wholeness. The repetitive bridge at the song’s conclusion creates a hypnotic and emotionally overwhelming experience, making it a profoundly moving and tear-inducing track for many listeners who have experienced similar traumas.

3. Forever Winter

“Too young to know it gets better / I’ll be Summer sun for you forever.” “Forever Winter” ventures into the sensitive territory of mental health with a poignant and empathetic perspective. This song is a stark reminder of the often-overlooked struggles with mental well-being. Whether interpreted as a reflection of personal struggles or concern for a loved one, “Forever Winter” resonates deeply due to its raw honesty and compassionate approach. The juxtaposition of upbeat instrumentation with profoundly sad lyrics is particularly effective, highlighting the often-hidden nature of internal battles. The song’s emotional weight is undeniable, making it a truly heart-wrenching listen that can easily trigger tears and empathy.

2. Soon You’ll Get Better

“Who I am supposed to talk to? What am I supposed to do, if there’s no you?” “Soon You’ll Get Better,” featuring The Chicks, is a song that many listeners, including Taylor herself, find incredibly difficult to listen to due to its raw emotional vulnerability. Inspired by Taylor’s mother’s cancer diagnosis, the song is a heart-wrenching portrayal of fear, helplessness, and the desperate hope for a loved one’s recovery. For those who have experienced the pain of losing someone to cancer or witnessing a loved one battle the disease, “Soon You’ll Get Better” is almost unbearably poignant. Taylor’s decision to rarely perform it live underscores its deep personal significance and emotional toll. The song’s simple melody and devastatingly honest lyrics create an intimate and profoundly sad listening experience.

1. Ronan

“Flowers pile up in the worst way, no one knows what to say about a beautiful boy who died.” Consistently cited as one of, if not the, saddest Taylor Swift song, “Ronan” is an emotionally devastating tribute to Ronan Thompson, a young boy who tragically lost his battle with cancer. Written from the perspective of Ronan’s mother, Maya, based on her blog posts, “Ronan” is a raw and unfiltered expression of a parent’s grief. Taylor’s empathetic songwriting captures the unimaginable pain of losing a child with heartbreaking clarity. A warning to first-time listeners: “Ronan” is an intensely emotional experience. Prepare for tears and allow yourself time to process the profound sadness evoked by this song. It’s a testament to Taylor’s songwriting ability to convey such deep empathy and heartbreak, making “Ronan” the pinnacle of sad Taylor Swift songs.

Did this list resonate with you? Are there other Taylor Swift songs that consistently bring tears to your eyes? Share your thoughts with us on our social media!

Written By: Kaitlyn Nicole