This isn't on the list but I feel like I should include it since this is kind of where it all started:
"Pale Kid Raps Fast"
"Pale Kid Raps Fast"
This video became what we call "YouTube viral". Before this, he was doing spoken word/slam poetry shows across the United States at college campuses and also competed in various spoken word competitions. Around the time this video became viral, he was also trying to make progress in his music career and the rest is history! Anyway...
"Hercules" - Watsky (2009) - This is a song I just started listening to more and more. It's actually about Watsky's family involvement in Hercules Inc., a chemical and munitions manufacturing company. While he's telling the story, he's also explaining his drive and determination to be "just like Hercules"...the Greek hero as well as the company...strong, successful and talented. I think he's accomplished all three of those things since he's recorded this.
"IDGAF" - Nothing Like the First Time (2012) - This is definitely the top of my list of songs I'll give to someone who has never listened to Watsky. It's just a light hearted romp that speaks the truth. There's not really much to say about it, it just has to be heard...and seen (the video is awesomely weird).
"Stupidass" - Nothing Like the First Time (2012) - This is a song I don't think a lot of people would include on this list but for some reason, I love it. The "some dudes'll front 'how do you do, mama?'" part just always gets me. The video is a little gross but I can appreciate it. Also, this song is one of the many references to his formally beloved Subaru...which he recently just gave away as a contest prize during press for x Infinity! I'm wondering if he's still going to talk about it in his songs just for traditions sake.
"Wounded Healer" - Nothing Like the First Time (2012) - Another one of my favorite songs by him and a top pick for songs I like to have people listen to when they've never heard Watsky before. The instrumental is a sample from Deer Tick called, "Baltimore Blues No. 1" and it's one of his very few samples he uses in his music (at least samples from music that is popular). When asked what inspired this song during a Reddit AMA he said: "my father's best friend committed suicide last year. they were both psychotherapists who got into the field to help others deal with problems they both had when they were younger. 'wounded healer' is a term my dad used to describe therapists with previous life trauma." He also has more about this in his new book How To Ruin Everything which is definitely worth a read and is inspiring and heartbreaking just like this song.
"Strong as an Oak" - Cardboard Castles (2013) - Whenever I feel like I want to just go back to bed and not deal with life or people, I listen to "Strong as an Oak." And then I can function as a human again.
"Moral of the Story" - Cardboard Castles (2013) - "But if you got a goal you gotta hold onto it that what hope is / If I didn't have it I would ask you where the rope is". Contrary to the lyric I just quoted, this is Watsky's "Loose Yourself" - it gets you hyped up and ready to do the things you're nervous to do. Whether it's a job interview, waking up in the morning or maybe it's both. "Moral of the Story" will make you feel like you can do that..."'till your arms fall off, till your abs get hard and your bone's all soft."
"Hey Asshole" (feat. Kate Nash) - Cardboard Castles (2013) - To be honest, this is just a cute, funny song and I don't have much to say about it. It definitely should be on the list because it's one of his catchier songs and there's a vast majority of music listeners who I think, would dig this. It also shows his versatility as a songwriter. Plus, it's featuring Kate Nash and she's pretty awesome!
"Whoa Whoa Whoa" - All You Can Do (2014) - Another great example of his songwriting as well as his rhyming skills. He does say in this song that his skills are "highly honed." I'll let you find out what the lyric before that is! He definitely toys with word play here - my favorite being: "I'll jump the freeway median, I'm savage/ Cause my mode is that I'm meaner than the average" also in reference to you know, Math. Oh yeah, also, also...I spy Bo Burnham!! I realized after watching this before writing this paragraph, dude is an instigator like whoa in this - he's giving George the gasoline, the lighter...he's just a big pyro in this, huh? And I'll also shout out Chinaka Hodge who is absolutely fantastic and the girl with George and Bo in the beginning. Hodge is a fellow Bay Area slam poet. She actually was featured on a song on Cardboard Castles called "Kill a Hipster", which is great and is very relatable to an almost 30-year-old who doesn't like to admit she's a hipster but totally is, and also makes an appearance on Watsky's new album ("Exquisite Corpse" - another great one).
"Never Let it Die" - All You Can Do (2014) - This is one of my favorite songs, period. Like, just in general. Similar to "Moral of the Story," it's a song I like to listen to when I'm feeling down or when I need a pick me up. I love the end where he says: "We won't surrender, we'll wipe the blood up with the White flag." So epic! The video is pretty great too!
"Tiny Glowing Screens Part 3" - x Infinity (2016) - Wow, I'm finally getting to x Infinity! This list turned out to be much longer than I thought, just like I thought the Ryan Adams list would be. Anyway, yes, there is a Part 1 and 2 of "Tiny Glowing Screens" and they're awesome, especially Part 2, which is a spoken word poem rather than a song. But "Tiny Glowing Screens Part 3" is probably one of the best introductions to an album I've ever heard. Again, it gets you pumped. You're like, "yes, let's continue this journey and listen to more music on this album. I'll pour us a couple more scotches."
"Talking to Myself" - x Infinity (2016) - This is a great example of Watsky showing his growth as he progresses as an artist. I feel like this song is what "Wounded Healer" evokes, like they're fraternal twins of each other, but "Talking to Myself" is written in a more general sense. The lyrics are so genuine and real, the day that Watsky is describing you could have had last week. I also love the "how ya feelin' today?" part in the background throughout the song. And again, the video is something to watch too. The dancer in the video choreographed this as well.
"Yes Britannia" - x Infinity (2016) - There hasn't been a video for this song released yet, but I hope there will be soon because it might shed some light on what exactly this song is about. A lot of people who are Watsky fans online are speculating it could be about a relationship he had with a British person, about a lawsuit he dealt with in England while he was performing during the Warped Tour in 2013 or it could be about both - the verses are interchangeable and it does seem like one verse could be about one story and the next verse is about another. So, who knows. But it's a great song - reminds me of something that would be on All You Can Do.
"Stick to Your Guns" (feat. Julia Nunes)- x Infinity (2016) - An important song in his discography. I'm not going to get political on this blog so I'll just let you listen to it and decide if you like it. Plus, Julia Nunes!
"Brave New World" (feat. Chaos Chaos) - x Infinity (2016) - I'm really into this song right now - it's put together so delicately but it doesn't sound delicate. The Chaos Chaos hook is awesome. And it again, shows growth in his lyrics and in his music. He's telling a story with his song and that is something a lot of musicians don't know how to do. It's not a requirement to be a good musician but it certainly helps.
Before I'm done writing this...I have to add one more...damn, it's so hard to make lists for me. I just want to include EVERYTHING! Just listen to Watsky, how about that?
It's an honorable mention from Nothing Like the First Time and is sampling Diddy & Dirty Money's "Coming Home" which is a guilty pleasure of mine...although I guess I'm not really too guilty if I just admitted it, am I?
"4 AM (Monday)" - Nothing Like the First Time (2012)