“After a person turns 21, most milestone birthdays are ominous reminders of our mortality. 30, 40, 50, 60. Potentially depressing moments in a person’s life.” – George Watsky, How to Ruin Everything

It is rare for someone at 30 to be able to say they’ve had an impact on millions of people’s lives. However, that’s not exactly the case for artists and other well-known public figures. An artist’s goal isn’t fame but instead self-expression. With that in mind, seeing as today is George Watsky’s 30th birthday, we thought it best to celebrate the 30 years of existence of one of our favorite artists with a list of his 30 best songs.

01. Sloppy Seconds

If there is one song that encapsulates what makes Watsky so special, it’s “Sloppy Seconds.” With earnest lyrics that alternate between playful and silly, serious and somber, and a fit-for-road trips tune that’ll be stuck in your head for weeks after listening, “Sloppy Seconds” secures its place as Watsky’s number one song. – Schyler Martin

Lyric highlight: “And there is not a single place that I would rather be. I’m fucked up just like you are, and you’re fucked up just like me.”

02. Cannonball

Along with his musical career, Watsky is an accomplished spoken word poet. “Cannonball” combines Watsky’s spoken poetry with gorgeous vocals from Stephen Stills and captures a beautiful story of young love. Honestly, there are no words to describe the magnificence of this song. Pop in your headphones, close your eyes, and let Watsky take you on a journey that feels as intimate and as genuine as any song I’ve ever heard. – Schyler Martin

Lyric highlight: “If I’m so brave, why does looking you in the eye take every ounce of my courage? I hang my face to the linoleum and count the freckles on the floor. All of us, all of us are a galaxy of tiny little storms.”

03. Talking to Myself

Watsky’s new album, X Infinity, is thematically darker and tonally more serious than anything Watsky’s done before. It’s a stunning feat, and “Talking to Myself” is a clear standout that explores loneliness, doubt, and the struggle to push through the dark times. – Schyler Martin

Lyric highlight: “As you got older there were days of cold surrender, days of shrugged whatevers folded in with days of shocking splendor. But as time advanced the lovely days were covered up from view by an advancing melancholy haze that hovered near the dew.”

04. Love Letters

The most defining skill of Watsky that’s usually on display is his mastery over the use of words. It’d be hard to find a better proof of the unique talent and voice he brings to the world of lyricism than in the verses of “Love Letters.” Here, in the song Watsky himself describes as his “ode to lyrics,” Watsky highlights the power of a musician’s or poet’s words, and celebrates those who use the art form as expression. His switches from celebrating other artists to thanking his fans to criticizing the superficialness of most popular artists today are seamless and he approaches each topic thoughftully. There isn’t really a more genuinely Watsky song out there. – Anton Reyes

Lyric highlight: “Cause every time I hear a line that shows me I’m not alone it’s saving me, cause I know that that’s a lifeline, like minds-”

05. Sarajevo

A song about a Muslim/Christian couple who were shot dead while fleeing Sarajevo during the Bosnian Civil War in 1994, Watsky’s “Sarajevo” is a love song that is personal and painfully relevant. It’s not often you get a love song that talks about religious prejudices that are seeded in political views and fear. Despite its rather sorrowful premise, the song stays true to the idea that romance is the defiance of limits. – Anton Reyes

Lyric highlight: “I’m not blind to the cycle, we’re pressed in the spine of a Bible, they define the divine by the title, but what did Christ say? To be kind to my rival”

06. Lovely Thing Suite: Conversations

In this song, another from X Infinity, Watsky recalls a conversation about death he had with his father as a child. “Conversations” feels like the embodiment of a late-night existential crisis. It’s big and scary and emotionally taxing, but it’s worth it. – Schyler Martin

Lyric highlight: “Although the thought of paradise is very nice, in my heart I know I don’t believe in magic, so I’m thinking maybe death is like eternal TV static.”

07. Cardboard Castles

The titular song of Watsky’s second studio album is what was in the mind of the person who coined “music to my ears,” or at least, I assume so. Like its main subject, “Cardboard Castles” is a well-made composition made up of unique parts that just make the whole better. And so is life in a way, the song suggests. One can easily commit a mistake or fall down in life, but with a strong a soul, that person can still be able to succeed. – Anton Reyes

Lyric highlight: “This life’s our greatest project, the journey’s all an art”

08. Wounded Healer

In what might be Watsky’s most heartbreakingly honest song, he writes about the death of his father’s best friend. A fitting guitar sample from “Deer Tick” elevates the song musically and gives it a sound that matches its melancholy lyrics. – Schyler Martin

Lyric highlight: “Yesterday night after dark, he carefully wrote his remarks, but everyone said what he put on his page so he threw it away and went straight from the heart.”

09. Whoa Whoa Whoa

One uniquely lovable quality of Watsky is his assurance in his own voice as an artist. Watsky’s most watched music video, “Whoa Whoa Whoa” is easily the most entertaining track on the album All You Can Do. Watsky, dropping bars at rapid fire pace, is borderline narcissistic in his approach, but further proves that he is solely humble and devoted to the word. – Anton Reyes

Lyric highlight: “I jump the freeway median, I’m savage cause my mode is that I’m meaner than the average like my teacher taught me, when I heard the crowd applaud I thought I was an atheist until I realized I’m a god.”

10. Hey, Asshole

With a gorgeous chorus sung by Kate Nash, Watsky delivers the kind of song that makes the world seem brighter, better, and generally more hopeful. Sometimes you’re unhappy for no real reason at all, but this is the kind of song that can help make things feel manageable. – Schyler Martin

Lyric highlight: “But when you take a punch, don’t you ever forget why you get up and you put one foot in front of the next.”

11. Stick to Your Guns

In this rousing response to gun violence, Watsky chronicles the cycle of a typical mass shooting. From the shooter’s perspective to the media’s sensationalized reporting to the inactivity of politicians in Washington to make meaningful changes, Watsky’s most political song is a representation of the many ways the United States fails victims of gun violence. – Schyler Martin

Lyric highlight: “Of course we know this situation is tragic, but take a minute to appreciate our fabulous graphics. We’ll be back in action with up to the second reports, after a couple of words from all our loyal sponsors of course.”

12. Never Let It Die

“Never Let It Die” emphasizes the importance of willpower and, as the title obviously suggests, how it shouldn’t be so easily lost. Watsky inspires solitude in what is his most telling song as an artist. He acknowledges the difficulties of building oneself up as an artist, the challenges of not compromising to the fame or the money, and the fulfilment one receives for chasing their passion. Watsky provides an insane amount of inspiration to keep one from not giving up. – Anton Reyes

Lyric highlight: “You might think that you’re ruined. You might think you’re defeated. If you love what you’re doing you’ve already succeeded”

13. Tiny Glowing Screens, Part 3

At its most basic, “Tiny Glowing Screens, Part 3” is just a perfect way to open an album. Its opening, aside from continuing the train of thought of the previous “Tiny Glowing Screens,” sets the stage thematically for what the listener is in store for in the rest of the album. It also features the most Watsky types of verses, which is why it being the one to announce the new album made the experience all the more exciting. At its core though, “Tiny Glowing Screens, Part 3” promotes the celebration of life in the moment. There’s no past, no future, no meaning in the small or big things, there’s just us and the present we have to celebrate. – Anton Reyes

Lyric highlight: “Just take everything ever and we are that times infinity”

14. Moral of the Story

Watsky fans knew what the moral of the story was before Rihanna had “work work work work work” blasting on the radio. “Moral of the Story” is the perfect motivational song. It’s impossible to resist the beat’s goal to get the listener hyped and every line of Watsky’s is entertaining enough to get you listening and hard-hitting enough to get you working. – Anton Reyes

Lyric highlight: “‘Cause waiting doesn’t work, and praying may not come through, and hoping doesn’t work. So I will be the one to.”

15. Strong as an Oak

In this insanely catchy jam, Watsky creates an anthem for everyone who has less money than they’d like to have (AKA everyone). If there’s one thing Watsky consistently does well, it’s point out a positive spin for a bad situation, and “Strong as an Oak” might be the greatest example of that skill. – Schyler Martin

Lyric highlight: “I’d rather be making the choices I’m proud of than chasing a mountain of money, but if that mountain comes to me, I’m climbing it.”

16. Little Slice

This is another track that proves the infinite amounts of positivity that Watsky has. “Little Slice,” the way I see it, is a nature song about how life is good and we should feel good because of that. It’s a great song to immerse oneself in on a roadtrip, in a field of grass, on a mountaintop, on a beach, or even when just watching the sunset from one’s bedroom. It features Watsky’s typically clever life analogies complimented beautifully by SkyHigh’s vocals and a variety of instruments. It will not fail to make you relax and settle in paradise. – Anton Reyes

Lyric highlight: “Don’t give a damn if I’m damp, I dance in the rain, I decided to celebrate like the sky is dumping champagne on me”

17. All You Can Do

Prior to the release of his essay collection How to Ruin Everything, I’ve always thought of “All You Can Do” as a unique Watsky track because of its self-reflection over a specific event in his life. Even naming the album, which mostly features grand and existential thoughts about life and/or the self, after it, a rather intimate and inward song, makes it stand out in a really special way. “All You Can Do” sits the viewer down with Watsky, and he lets us know that past mistakes don’t define your life. – Anton Reyes

Lyric highlight: “I try to jump and spread my wings like I’m a bird of prey, but I hit the earth and break a mothafucka’s vertebrate (hey)”

18. Don’t Be Nice

Following suit of “Whoa Whoa Whoa,” “Don’t Be Nice” features the same rapid fire pace as well as less-than-humble approach, but still all coming from a place of love for artistic expression. “Don’t Be Nice” is Watsky without a filter, both literally and metaphorically. He wastes no time and breath delivering his quick verses about how he hates superficiality and isn’t afraid to say it. – Anton Reyes

Lyric highlight: “If you’re Jesus then we break bread. If you’re Beavis then we butt heads”

19. Lovely Thing Suite: Knots

Accompanied by a stunningly beautiful piano track, “Knots” tell the story of an accomplished pianist’s suicide. The song begins as haunting and lovely and builds to a crescendo that is so haunting it’s almost unbearable. Put simply: this song is a work of art. – Schyler Martin

Lyric highlight: “What a strange and impossible sum: To be old while to still be so young. To have sung before speaking a word. To be heard, to be hailed, then to fail. To be done.”

20. Bet Against Me

“Bet Against Me” is Watsky’s most prideful song so far. He isn’t as blatant in his delivery of his lines than in the other two appropriately self-indulgent songs on the list, instead focusing on a steady build of the beat and repetition. The song doesn’t fail to let the listener know that Watsky is proud of his achievements as an artist. – Anton Reyes

Lyric highlight: “I’m swimming though it, I’m swallowing fluid. Knew I had to do it so I grew like a million gills, cause evolution is kill or be killed”

21. Chemical Angel

Perhaps the easiest interpretation of Watsky to gather from this list’s review of his greatest hits is that he doesn’t like not staying true to himself. It’s a relatable principle to have, but Watsky brings in a new perspective because of his dealings with pharmaceutical conditioning. It’s a topic of a couple of his songs that he hates how his medicine turns him into what is basically a zombie, and in “Chemical Angel,” he gets to voice out that frustration and his feelings after recently stopping his medication. It’s a moving song with beautiful, classic vocals and drums that appropriately interrupts the easiness of the song. – Anton Reyes

Lyric highlight: “I know I’d rather lose my life than have to lose myself”

22. The One

One of Watsky’s more playful songs, “The One” represents that stage of not being in a relationship where one is deprived but still patiently waiting for a good partner. It’s generally not so serious, but it has this bitter undertone as well. Perfect for all the single ‘Ones’ out there. – Anton Reyes

Lyric highlight: “All the faker single ladies twerkin’ to Beyoncé, every single one of ’em is somebody’s fiancée”

23. Exquisite Corpse

This nearly 10-minute song tells a story fitting of a feature film. When zombie robot clowns take over the earth, rapper Watsky, Dumbfoundead, Grieves, Adam Vida, Wax, Rafael Casal, Daveed Diggs, and Chinaka Hodge struggle to survive and find hope in an apocalyptic world. With this lineup, you know this song has to be special, and with lyrics alternating between humorous and terrifying, and unforgettable guest verses, it certainly is. – Schyler Martin

Lyric highlight: “A visitor from the surface stole a garlic roll from Dave and Busters, and I butchered the buster in his sleep just to lick his fingers for butter.”

24. Going Down

It’s a perplexing moment when the song starts and reveals itself to be about oral sex. The astonishment increases all the more when halfway through the song, Watsky describes not only going down on a woman but on a man as well. Wastky is all about pleasure here, and he admits he gets pleasure from providing pleasure to other people. Since that’s the case, it’s rather disappointing that, due to the social norm, he can only provide pleasure to one half of the population. This is the weirdest Watsky song I’ve ever listened to or probably will listen to, but it’s the one I find myself most wanting to preach and play around. Watsky definitely proves that unconventional, highly inappropriate, but progressive and endlessly entertaining songs are the new kind of sexy. – Anton Reyes

Lyric highlight: “If I could get with it I’d have a wider ocean I’m fishing in but I’m inhibited by my social conditioning”

25. Brave New World

Like “Exquisite Corpse,” “Brave New World” shows of Watsky’s sci-fi side as he raps about the unbelievable state of the world we live in. It’s an epic anthem of disbelief, fear, and foreboding dread. – Schyler Martin

Lyric highlight: “You wanna flee the reaper but they’re bombing the city and the single haven to creep in is the slaughterhouse.”

26. Tiny Glowing Screens, Part 1

In this anti-technology track, Watsky yearns for a time before we were all glued to our screens, before people watched concerts through cell phones. The message is relatable, the lyrics are slick, and the beat is memorable. What’s not to love? – Schyler Martin

Lyric highlight: “I can’t tell our little victories from epic fails. It’s either heaven or hell and I can’t make heads or tails.”

27. Yes, Britannia

The world was not made for long-distance relationships, and while it’s a sad and confusing experience to go through, I’m appreciative that Watsky was able to disclose his thoughts and feelings toward it. Like the topic it covers, “Yes Britannia” is sad and confusing. Although Watsky stays true to his principles of wanting a true relationship, he goes back and forth a lot within his verses citing reasons to both stay and go. Most of the song sounds as if he’s conflicted and talking with himself, many thoughts coming from different places (literally, some lines in the outro overlap and come from different areas of the speaker). It’s a song that spends a lot of time deciphering yet still arriving at no conclusion. – Anton Reyes

Lyric highlight: “Like sayonara, I don’t know if I can try tomorrow. Am I supposed to say a hallelujah, smile I knew ya, and go on my way?”

28. Stupidass

If there’s anything this list has taught me, it’s that Watsky is all about self-love. “Stupidass” is a song about owning your mistakes and having no regrets, and damn is it rad. – Schyler Martin

Lyric highlight: “So I moved to LA, to the land of milk and self hate, but one day, I’ll strip and then strut buck down the sunset strip as it was a runway. I’m thinking maybe Sunday.”

29. Midnight Heart

Most Watsky songs are mixed with crystal clear lyrics, but “Midnight Heart” is different. It’s noisy and stimulating and hype as hell. After a list full of mostly existential songs, “Midnight Heart” is a great excuse to jump around and rage. – Schyler Martin

Lyric highlight: “I took a difficult look in the mirror, and I checked in the rearview. Objects are never what they appear. The past tends to look crooked from here.”


After a list of deep existential songs, it feels fitting to end with the polar opposite, because that’s just the kind of range Watsky has. “IDGAF” is goofy, fun, and mostly ridiculous, but I dare you to listen to it without dancing. – Schyler Martin

Featured Image: Steel Wool Media/Welk Music Group