Top 20 Songs That Make You Dramatically Look Out the Window

#20: “Teardrops on My Guitar” (2007)

Taylor Swift


In the early days of her career, Taylor Swift blended country and pop music into something many audiences could love. This particular track showcases her early grasp of relatable lyrics, strong hooks, and memorable melodies. “Teardrops on My Guitar” follows Swift through a case of unrequited love. Unable to confess her feelings, the singer sends us all into flashbacks of our early crushes. It’s about the wonders and pitfalls of falling for someone and it never fails to make us misty-eyed. For anyone that grew up with this single, they’re instantly transported back to a time and place where emotions run high.

#19: “I’m With You” (2002)

Avril Lavigne


She could do pop punk, but the Canadian artist could also do ballads. “I’m With You” gives you the sense that the singer is struggling without a relationship. It’s an unapologetic look at the need for companionship and guidance that seems to complicate our lives. The strings give this composition weight, transporting you to a night in your past that you wish you could forget. Lavigne’s impressive high notes usher listeners through a tornado of nostalgia and tears. Even if you’re not a teenager, you can find something to inspire you about this unforgettable track.

#18: “Wonderwall” (1995)

Oasis


Of all the Britpop anthems, this one might be the most famous and widely-played. And “Wonderwall” hasn’t lost any of its power to send shivers down our spines. Oasis’s huge hit can be interpreted in several ways that relate to topics such as family, friendship, or romance. It makes you remember the people you need the most when you’re down, asking for someone to come and save you. “Wonderwall” gives listeners plenty to imagine while they’re singing along. Liam Gallagher’s perfect performance is a key reason why this song is so impactful, as it transfixes from start to finish.

#17: “Fake Plastic Trees” (1995)

Radiohead


From the band’s second album, “Fake Plastic Trees” examines the problems of modern society, using memorable phrases to explore the fakeness of life. Thom Yorke’s tremendous voice digs right into your soul, forcing you to consider how artificial aspects of our lives might affect our relationships. The song doesn’t hold back as the singer’s voice climbs and the surrounding production hits hard. It might start like a softer acoustic track, but it gradually builds until you’re completely engulfed in Yorke’s staggering vision. Radiohead is known for their fair share of melancholy material, but this one alters your mood in extraordinary ways.

#16: “Heaven or Las Vegas” (1990)

Cocteau Twins


Every song from this band is a force unto itself. The title track from the monumental album “Heaven or Las Vegas” is no different, bringing together their mastery of dream pop with a captivating and wonderful arrangement. Elizabeth Fraser’s one-in-a-million vocals reverberate through a magical soundscape. You might not always be able to understand her, but you’ll definitely be captivated by the engaging melody. The amazing blend of instruments gives the song an angelic, heavenly feel. Fraser and her talented bandmates are more than capable of wowing listeners, creating an unforgettable experience that completely takes hold of you.

#15: “Boulevard of Broken Dreams” (2004)

Green Day


Off of their smash hit album “American Idiot,” “Boulevard of Broken Dreams” is a portrait of a tortured soul. Billie Joe Armstrong’s words perfectly convey the feeling of intense isolation. The deliberate pacing, haunting lyrics, and hard rock sound combine to make a dramatic experience. The song’s place in the band’s larger rock opera only makes it that much more effective. The Grammy-winning single combines the catchiness of the group’s best songs with the gothic majesty of their 2000s output. If you find yourself looking out a window, you’ll be thinking about all the times you felt alone just like this character.

#14: “Changes” (1998)

2Pac feat. Talent


One of the superstar rappers of the 1990s, Tupac Shakur’s light burned bright during his brief career. “Changes” was released after the performer’s death and brilliantly showcases his staggering voice. And including the sample of Bruce Hornsby’s “The Way It Is” is the perfect way to highlight the emcee’s message. The insightful and incisive lyrics unleash Shakur’s thoughts about the inequities of the world. The rapper’s timeless takedown of war, racial injustice, and hate hasn’t lost any of its power - or, sadly, its relevance. It could’ve been recorded yesterday, giving audiences of all ages, backgrounds, and beliefs a compelling thesis to consider.

#13: “All by Myself” (1975)

Eric Carmen


Some might see it as a bit cliched, but this 1970s ballad is unmistakably moving. You can’t help but feel the intense emotion that powerfully drives this chorus. Eric Carmen’s tune has been covered by all kinds of performers, giving each individual artist the freedom to interpret its greatness. It’s also the perfect song to use for a sad moment in movies like “Bridget Jones’s Diary.” In an ultimate tribute to loneliness, Carmen’s heartfelt delivery brings together the swirl of feelings that come from being by yourself. The artist taps into a universal problem, sending you on a cathartic and sometimes depressing journey.

#12: “Adam’s Song” (2000)

Blink-182


Many tracks in this band’s catalog are fun and irreverent. “Adam’s Song” is the furthest thing from that, describing the ways that our minds sabotage ourselves. In one of the group’s most impressive compositions, Mark Hoppus sings some chilling lyrics about someone that might be considering drastic measures. Anyone that struggles with depression will undoubtedly find something to relate to here. While trying to find hope in a seemingly hopeless situation, the track does give listeners a sense that they can also make it through tough times. It’s a compelling track about mental health that’s a beautiful reminder to seek help when you need it.

#11: “Breakaway” (2004)

Kelly Clarkson


We all sometimes need an escape from one aspect of our lives or another. “Breakaway” describes this struggle with a tale of a small-town girl dreaming of becoming something much closer to her wildest dreams. Kelly Clarkson’s vocals shine in a moving tale of hope, yearning, and redemption. The lyrics and performance lift you out of any funk, reminding you to reach for the stars, which is something we all need. Clarkson’s staggering talents also shine in this well-written song. It might even inspire you to get up off the couch and change your life right now.

#10: “The Boys of Summer” (1984)

Don Henley

In one of his radio staples, Don Henley looks back at the highs and lows of a nostalgic romance. The singer, like many of us, contemplates getting their old flame back and returning to the glory days. We both know that it’s never possible to do everything the same way again, making these lyrics especially melancholic. Henley can’t seem to let it all go as he discusses the difficult relationship we all have with the past. Leave it to this Eagle to create one of the most bittersweet summer anthems, with a lifetime of regrets packed into a masterpiece.

#9: “Heroes” (1977)

David Bowie

Always trying out new sounds, Davie Bowie beams in from outer space with this ethereal track featuring some stunning guitar work from King Crimson’s Robert Fripp. Adding Brian Eno’s input to Fripp’s contributions results in a final product that will have you spinning out with joy, confidence, and maybe even a few inspirational thoughts. Bowie’s lyrics create a romance that seems to be hanging on despite the struggles and pressures of the outside world. We might not all feel like heroes, but this track makes us want to fight for our dreams. It also features one of the artist’s most passionate vocal performances. As his voice gets louder, this groundbreaking work lifts off and takes our imaginations beyond the stars.

#8: “Purple Rain” (1984)

Prince and the Revolution

Prince was arguably never better than on “Purple Rain” - and that is saying a lot! “Purple Rain” is a love song the performance and production of which elevates it to a whole new level. Within the first few seconds, the track sets the mood in a way that few other ballads could. It’s haunting, soulful, and infused with all of the heart wrenching emotions of a drama. You’re instantly placed in the performer’s perspective as he takes the title image and makes it feel real. Few singers can write, vocalize, and perform with such raw intensity. His expertise in all areas of music allow him to make the impossible possible, allowing the audience to access the deepest parts of themselves.

#7: “Fast Car”

Tracy Chapman

In her first signature hit, Tracy Chapman gives her all to a moving track about getting out of a bad situation. She sings about both the hard times she’s experiencing and her hope for the future in a way that is relatable and at times painful. Chapman’s guitar helps lull you into a hypnotic state as her voice guides you through a dramatic tale about possible redemption. It’s incredible storytelling that has inspired decades of artists. With a timeless sound, the performer has been covered by many admirers of various music genres. This goes to show that her words and music is a universal testament to dreamers of all kinds.

#6: “Hallelujah” (2007)

Jeff Buckley

On this classic recording, Jeff Buckley channels Leonard Cohen for a memorable musical journey. His angelic voice carries you to a meditative place, with the poetic lyrics painting an abstract look at the intensity and complexity of love. Cohen’s original was already an iconic piece that’s only heightened by Buckley’s performance. It might be the finest cover of “Hallelujah,” giving the tune an unmistakable energy that doesn’t quit. There’s such a soothing quality to this song that manages to be dreamlike, despite some disturbing imagery in the lyrics. You’ll also find plenty of amazing metaphors to contemplate but Buckley’s performance will ultimately soothe any ruffled feelings.

#5: “Hurt” (2003)

Johnny Cash

Near the end of his life, Johnny Cash recorded a cover of this Nine Inch Nails song which became a eulogy of sorts for his own life. “Hurt” is among the more emotional recordings of his career, using the lyrics to question his past regrets and mistakes. The production puts you into the mood of an aging man, forcing you to confront the same topics. Trent Reznor’s original composition easily translates to the country artist in this graceful and inspired production. Cash couldn’t be better, giving his all to a track that’s a painful but healthy reflection on what really matters.

#4: “Both Sides, Now” (1969)

Joni Mitchell

In one of her most legendary songs, Joni Mitchell pours her heart out about gaining a different perspective on life. The song includes some clever metaphors and astonishing imagery that’ll be in your mind for hours. Mitchell’s poetic phrases about love stand out as some of her finest writing ever. It’s hard not to feel something as the artist reaches the chorus, sending listeners through a sentimental vortex. Her carefully-crafted lyrics and melody delicately explore the lessons we learn from life experience. That’s not all however, because the track works on so many levels that you’ll have to return to it year after year for new insights, as Mitchell herself has done.

#3: “Imagine” (1971)

John Lennon

For his iconic song “Imagine,” John Lennon proposes an idea of a society free from religion, conflict, or hunger. Lennon’s controversial message is both beloved and critiqued to this day. The somber and evocative piano part slowly guides you through the singer’s mind. The former Beatle lays out his case, asking listeners to consider whether or not the scenario he envisions is possible. He gives you the questions without pestering you to have the answers, encouraging you to think about the possibilities of the human race. Whether or not you agree with the message, you have to admit that the performer gives you a thought-provoking listening experience.

#2: “Landslide” (1975)

Fleetwood Mac

Thankfully for us, the members of Fleetwood Mac found a way to channel their sometimes toxic and intense emotions into classic songs. “Landslide” is just one example, showcasing Stevie Nicks’ singular writing talents. It’s all about the complicated feelings that arise when you’re on the cusp of a major shift. While we might be stuck in one phase of our lives, we might also be thinking about making a profound change. It’s difficult not to examine your own life when you’re listening to this song. Nicks has a knack for delivering her personal truth while leaving room for the audience to ponder their own future.

Before we unveil our top pick, here are a few honorable mentions.


“Vincent” (1972), Don McLean
The Folk Tribute to a Tortured Artist Never Fails to Make Us Shed a Tear


“I Still Haven’t Found What I’m Looking For” (1987), U2
The Gospel-Tinged Track Tackles the Insatiable Quest for What We All Need in Life


“My Immortal” (2003), Evanescence
A Moving Portrait of Grief Sung by the Incomparable Amy Lee


“I’m Just a Kid” (2002), Simple Plan
The Pop Punk Band Reminds the Kid in Us That We’re Not Alone


“Alone” (1987), Heart
The ‘80s Power Ballad Tugs the Heartstrings Exploring the Complexity of Romance

#1: “A Day in the Life” (1967)

The Beatles

Along with being the final track on the “Sgt. Pepper’s” album, “A Day in the Life” might represent the finest collaboration between John Lennon and Paul McCartney. You get both the introspective side of Lennon and the brighter side of McCartney. With psychedelic and pop production, it makes you reconsider your daily routine and you might even rethink your life. The whirlwind ending also demonstrates once again that this band was way ahead of their time. With the climactic chord, this musical epic carries you away with a slew of provocative thoughts. It’s an at-times harrowing song that makes the listener question what they are and should be doing with their life.



Did we miss your favorite icon’s most thought-provoking song? Let us know in the comments below.