10 Taylor Swift Songs Guaranteed To Make You Cry

Taylor Swift has built a career on crafting songs that resonate deeply with listeners, often tapping into universal emotions of love, loss, and heartbreak. Her masterful storytelling and poignant lyrics have an uncanny ability to evoke tears. While many Taylor Swift songs carry emotional weight, this list dives into the top 10 tracks that are almost guaranteed to bring on the waterworks. Prepare yourself, and let’s explore the saddest Taylor Swift songs that hit right in the feels.

10. Fifteen

Starting our list is “Fifteen,” a song that encapsulates the bittersweet nostalgia of youth and the painful lessons of first love and heartbreak. The lyric, “I found time can heal most anything, and you just might find who you’re supposed to be,” offers a comforting message of hope and resilience. “Fifteen” resonates because it taps into a universally relatable experience: navigating the awkwardness and vulnerability of adolescence. It reminds us of a time when emotions were raw and every heartbreak felt world-ending. The sadness in this song isn’t just about the past pain, but also the reflection on how far we’ve come and the realization of our own growth since those formative years. It’s a poignant reminder of youthful naivety and the journey of self-discovery.

9. All Too Well

“All Too Well,” especially the extended 10-minute version, is a masterclass in songwriting and emotional storytelling. With lines like, “I’d like to be my old self again, but I’m still tryin’ to find it,” the song delves into the lingering pain and confusion after a significant relationship ends. What makes “All Too Well” so impactful is its vivid imagery and specific details that paint a picture of a passionate but ultimately doomed romance. Listeners can easily project their own experiences onto the narrative, making the emotional impact even stronger. The rawness and vulnerability in Taylor’s voice, combined with the heartbreaking lyrics, create an atmosphere of intense sadness and longing that is hard to shake off. It’s a song that captures the messy, lingering aftermath of a love lost and the struggle to move on.

8. Tolerate It

“Tolerate It” explores the quiet desperation of feeling unappreciated and undervalued in a relationship. The lyric, “Gain the weight of you then lose it, believe me I could do it,” speaks to the exhausting effort of trying to earn love and recognition from a partner who is emotionally distant. This song is particularly heartbreaking because it depicts a slow burn of sadness, not a sudden dramatic breakup. It’s about the painful realization that your efforts are not reciprocated and the slow erosion of self-worth that comes from being in a one-sided relationship. The bridge of “Tolerate It” intensifies the emotional weight, making it a truly gut-wrenching portrayal of loneliness and longing within a relationship. It resonates with anyone who has felt unseen or unheard by someone they love.

7. Never Grow Up

“Never Grow Up” tugs at the heartstrings with its tender reflection on the fleeting nature of childhood and the anxieties of adulthood. The line, “It’s so much colder than I thought it would be, so I tuck myself in and turn my night light on,” perfectly captures the vulnerability and fear of facing the world alone. This song evokes sadness through its longing for simpler times and the innocence of childhood. It speaks to the universal desire to hold onto those carefree days and the fear of the responsibilities and complexities of growing up. “Never Grow Up” is a poignant ballad that resonates with anyone who feels overwhelmed by the pressures of adulthood and yearns for the comfort and security of childhood. It’s a reminder of the bittersweet passage of time and the preciousness of youth.

6. Marjorie

“Marjorie” is a deeply personal and universally relatable tribute to Taylor Swift’s late grandmother. The lyric, “I should’ve asked you questions, I should’ve asked you how to be,” expresses the regret and longing that comes with losing a loved one and the realization of all the unsaid things. This song is profoundly sad because it deals with the raw grief of loss and the enduring impact of someone who shaped your life. The specific details and memories shared in the lyrics make the song incredibly intimate and emotional. The inclusion of Marjorie’s opera vocals in the outro adds another layer of poignancy, making it a deeply touching and tear-inducing tribute to familial love and loss. It’s a song that reminds us of the importance of cherishing our loved ones and the lasting impact they have on our lives even after they’re gone.

5. Bigger Than The Whole Sky

“Bigger Than The Whole Sky” is shrouded in ambiguity, allowing listeners to project their own experiences of loss and grief onto its melancholic melody. The line, “I’m never gonna meet what could’ve been, would’ve been, what should’ve been you,” speaks to the emptiness and what-ifs that accompany profound loss, whether it’s the loss of a person, a dream, or a part of oneself. The song’s power lies in its gentle, ethereal sound and Taylor’s soft, mournful vocals, creating an atmosphere of quiet devastation. It’s a song that acknowledges the immensity of grief and the feeling that a part of you is missing. The beauty of “Bigger Than The Whole Sky” is in its open-endedness, allowing it to become a vessel for individual sorrow and a source of comfort in shared human experience of loss.

4. Would’ve, Could’ve, Should’ve

“Would’ve, Could’ve, Should’ve” from the Midnights album is a raw and unflinching exploration of regret and the lasting scars of a past relationship marked by manipulation and exploitation. The lyric, “God rest my soul, I miss who I used to be,” encapsulates the profound sense of self-loss and the lingering trauma of such experiences. This song is particularly sad because it confronts the long-term impact of toxic relationships and the struggle to reclaim oneself after being deeply hurt. The repetitive bridge at the end amplifies the feeling of being trapped in a cycle of regret and pain, making it an emotionally draining but powerfully cathartic listening experience. It’s a song that gives voice to the silent pain of those who have been deeply wounded by betrayal and the difficult journey of healing and self-reclamation.

3. Forever Winter

“Forever Winter” is a poignant and empathetic portrayal of struggling with mental health and the helplessness felt by those who care about someone battling inner demons. Despite its upbeat instrumentation, the lyrics, particularly “Too young to know it gets better / I’ll be Summer sun for you forever,” reveal a deep undercurrent of sadness and concern. The juxtaposition of the cheerful music and the somber lyrics intensifies the emotional impact, highlighting the often-hidden struggles of mental illness. “Forever Winter” is heartbreaking because it speaks to the pain of watching someone you love suffer and the desire to protect them from their own darkness. It’s a song that promotes empathy and understanding for those facing mental health challenges and the importance of offering unwavering support.

2. Soon You’ll Get Better (feat. The Chicks)

“Soon You’ll Get Better,” featuring The Chicks, is a devastatingly honest and vulnerable account of Taylor Swift’s fear and helplessness during her mother’s cancer treatment. The line, “Who am I supposed to talk to? What am I supposed to do, if there’s no you?” lays bare the raw panic and dependence on a loved one facing serious illness. This song is incredibly difficult to listen to because it taps into the universal fear of losing a parent and the agonizing uncertainty of serious illness. The simplicity of the melody and the rawness of Taylor’s vocals amplify the emotional weight of the lyrics, making it a truly heart-wrenching and deeply personal song. It’s a testament to the power of family bonds and the overwhelming emotions that come with facing the potential loss of a parent.

1. Ronan

Topping our list of saddest Taylor Swift songs is “Ronan,” a song that is almost universally acknowledged as her most emotionally devastating work. “Flowers pile up in the worst way, no one knows what to say about a beautiful boy who died,” are lyrics that cut straight to the heart, depicting the unbearable grief of losing a child. Written from the perspective of Ronan Thompson’s mother, Maya, about her son’s battle with cancer, “Ronan” is a raw and unfiltered expression of a parent’s unimaginable pain. This song is profoundly sad because it deals with the most tragic loss imaginable – the death of a child. Its unflinching honesty and heartbreaking details make it an incredibly difficult but important song to listen to, serving as a powerful tribute to Ronan and a testament to the enduring love of a parent. Prepare for uncontrollable tears if you choose to listen to this song.

Did this list bring on the waterworks? Are there any other Taylor Swift songs that you find equally heart-wrenching? Share your thoughts and connect with fellow fans on our social media channels!