If I had to wager a guess, I’d say that the last four years of my life have boiled down to two essential activities: working and lounging around listening to music. I own many platforms to do so, because I am a glutton for blowing wads of cash on many mediums of entertainment.

I do this because I don’t really watch TV anymore. I use my days off to sit around listening to anything that catches my ear (and watch skate videos, but that’s not today); and if nothing does, I have no shortage of catalogues to dig through. I’ve got terabytes of music, mostly leftovers when I was in high school and college, and wrote for any number of blogs with no concrete audience. Some of the songs from that era of my life is on this list, surprisingly (more shockingly because I’ve never had my iTunes crash, or reset, in 10ish years of being my primary media player).

These ten songs are a decent representation of my growth as an audiophile, from the backpack rap that bumped in my PT Cruiser towards the end of high school, to my current state as a guy who embraces the bliss of ignorance and pomp of pop music, as wide-ranging as the genre is.

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10. Crave You featuring Giselle by Flight Facilities

This is a song once featured on the very short-lived, and very not-that-great-in-retrospect HBO series, How To Make It In America. I loved that show, mostly because of Lake Bell’s wonderful breasts, and for the fact that it had a phenomenal soundtrack that wasn’t completely dominated by one of its stars, Kid Cudi.

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9. Vibrate by OutKast

To say that this is my favorite OutKast (kinda) song would be an understatement of the greatest degree. When I saw them perform in Atlanta a few years back, there was this odd interlude in their set when they broke off into the Speakerboxxx/The Love Below portion of the Kast timeline, and Three Stacks did about a minute and a half of this track. I almost cried.

8. Devil in a New Dress featuring Rick Ross by Kanye West

I defy anyone reading this to find a better verse in Rick Ross’ career than the one he lends to this track. It follows what is, arguably, one of the best instrumental pieces on any Kanye album in Mike Dean’s guitar solo. It’s six minutes of pure decadence and high-pitched Smokey Robinson sampling. It still blows my mind that people think Monster is the best song on MBDTF because of some lady’s patois.

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7. Self Control by Frank Ocean

The fact that this song is this far up in rotations in such a short amount of time should speak volumes about how much I fanboy’d for Blond when it dropped. What’s odd is that I’m still not sure what it is about the song that draws me in. It could be the Yung Lean bridge, or the neo-blues in the guitar riff, or the tortured feeling you get from the last three lines of Ocean’s second verse: “I came to visit cause you see me like a UFO/That’s like never, cause I made you use your self control/And you made me lose my self control, self control.”

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6. Jersey by Future

So, I can’t find the original on YouTube for whatever reason, so bear with me. I love this song because of one single, solitary line from Future: “I like the smell of that money when it burn.”

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It is a literal representation of the gaudy, unreserved state of current hip-hop, where mixtape rappers who get multi-million dollar deals off of one viral song can throw bands at chains and cars. This song is on a mixtape that pretty much skyrocketed Future’s career and gave Drake a push in the South. But this song is the highlight for me, because while it’s three minutes of talking about codeine fueled nights, it’s Future giving us the blueprint to staying relevant in a fluid industry.

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5. Quick And To The Pointless by Queens of the Stone Age

What’s odd to me with this track being so far high on this list, is that I’m a MASSIVE Josh Homme fanboy. Ginger Elvis is a personal hero of mine, but he’s not on lead vocals on this song, that would be Nick Oliveri (who I miss dearly). This is probably the most punk-centric track Queens have put on any one of their albums, and it’s very short and sweet.

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4. White by Frank Ocean

Oh, look, another Frank Ocean song!

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This is the only standalone song the guy had on the only “official” Odd Future album that is on record. It’s simple, it’s sincere, and a tad bit trippy. It was extended on Ocean’s solo debut, Channel Orange, a few months after this release with a little help from John Mayer, which took one simple key chord, and added some sultry guitar riffs.

3. Sunshine by Lupe Fiasco

I remember hearing this song for the first time in junior year of high school and being blown away that a guy could get away with a Super Mario reference to end a verse. This track hasn’t aged very gracefully, though. While I believe the beat is still on point, and the simple Diana Ross sample is a classic, Lupe’s falsetto-ish hook is tough to get through.

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2. Oldie by Odd Future

This is a ten minute mob-track that has the second most plays of any song I’ve ever thrown into my iTunes. Here’s everything I love about this:

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- Tyler’s opening verse might just be the best one he ever put down, he acknowledges everything about how he’s just a dude who fucks around with beat engineering programs and watches Dexter

- Hodgy’s knowledge of Greek mythology

- Left Brain doing real work on the mafioso lines, and throwing bitches in aqueducts

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- Mike G’s verse is so smooth it hurts, like a room full kittens in rap form

- Domo Genesis has a bar in his verse: “Big wheel was a big deal with the water glocks.” It is quite possibly my favorite line in any rap song, ever. EVER.

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- Frank Ocean, again, with a little bit of everything, including breaking the news of him coming out, before he actually came out

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- Jasper acknowledging he is not a rapper, but trying anyway

- Earl Sweatshirt, fresh from his hiatus, gives us a Ferris Bueller line, in what I believe is one of the five greatest verses of the last 10 years (but that’s another post for another day)

- Tyler’s ender is a stamp on OF’s legacy. Even though it didn’t really take long for the massive group to fade, they defined an era in which creativity wasn’t merely boxed into where you came from, or what you had to say, but how you said it.

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1. 50 Ways To Make A Record by Kid Cudi

This is at the top of the playlist because of Paul Simon. I grew up listening to Paul Simon, among many others, while my mom would clean the house on weekends. The first time I heard this, I almost cried. It was like an instant time machine back to sitting on the floor of my room playing with Hot Wheels, while the smell of lemon Pledge floated through the house.

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No matter where Cudi is at this point in his career, I can honestly say there’s no artist on the planet who throws me through time warps like he does, and this song does the best job at it.