A Song a Fay: Lent 2025

Pre by Earl Sweatshirt

Ahhhh…good old freshman year of high school lore.

This album is so important, man. At least to me. “Doris” came out my freshman year of high school. I’m fortunate enough that one of my absolute best friends is a wizard when it comes to music. He just loves it and loves all aspects of it. He’s blessed me with some great music and we’ve had great conversations that come with it.

He made me feel bad that I thought about downloading the album illegally because it wouldn’t give earl his well earned coin. I waited patiently for it to drop. I remember going up to my attic in my house and seeing that it had finally come.

It’s special because I have so many vivid memories associated with it.

I chose this song specifically because my friend was upset that Earl didn’t actually open on his own album. I actually can’t believe I remember that conversation, but it’s one that I cherish to this day.

I remember playing this while playing Pac Man World 2 (great game btw) with my brothers in my room. The new IOS update had just come out when the blue texts were invented. What a time.

I actually had sent my HS girlfriend one of the songs on this album (Chum) as an attempt to look trendy as if I didn’t listen to whatever everyone else was listening too. She actually ended up really liking it. Pro tip – if you ever send your girl an earl song and she likes it, you gotta keep her.

This, through and through, is a fantastic album IMO. I love looking back on this moment in time. It reminds me how lucky I am to have a friend like I do, and all the memories I carry alongside with it.

Pool House by Willis

I would imagine there was a big audience (in this case a small audience…I don’t actually know how many people read this) that partook in the Chicago festivities this weekend.

If you’re anything like me, you’re in dyer need of a pick me up song. Or a yellow gatorade.

I discovered WILLIS a few summers back. They have a great vibe – also a great sort of jam sesh/interview on youtube you should check out.

I usually put on WILLIS during my Monday afternoon walks, but today they were much needed. I like the overall reminiscent theme of this song. Murphy Billings looking back on fun times in a pool house while coming to the grips of the fact that live continues, and we must too.

Action follows inspiration. It was a brutal Sunday weather wise after an immaculate Saturday. I went back to the suburbs to be around good company. It was another window of time where all of my siblings were together. Were on much different paths now – my oldest had a kid, older brother having a kid, older(ish) in wisconsin, and my younger brother in college. As you could imagine, those windows become more narrow to get through.

We enjoyed way too much corned beef and shared some laughs. I turned on a few hours of House to close out the night.

The sun eventually came out after snow. Just comes to show that this too shall pass, so we might as well enjoy it.

Find Your Love by Drake

I was going to write a Saint Patrick’s themed blog in honor of the festivities here in Chicago.

However, I was watching the B1G tournament last night and I got a Facebook facetime call from my mom (she’s an android user, I know).

She never does this – only calls. When I answered she said “oh, you don’t want to see me?” and then I realized I had to open the Facebook app on my phone to activate my camera.

When she was able to see my face, her expression was as if she was the first caveman to see fire. She was so happy to see me, let alone have a conversation.

And so, today, I’m going to shout out my mom real quick.

---

My mom used to drive a Honda Odyssey to haul her five kids. Lots and lots of memories in that van. Actually, one of my first times actually driving a car happened to be that van. I had just got my permit and I asked my mom if we could get lunch. She let me drive all the way to Chipotle and back. My freshman year self made an odyssey feel like a Maybach.

I remember this because my ex girlfriend was having a big party that same night. We had just broken up, I was rattled there was a party I would attend that night. However, in that blip in time I was able to enjoy a nice ride with my mom.

I was in middle school when Drake had dropped Thank Me Later. It’s an album he doesn’t praise much despite its hits. That 2009 Drake was special. I’d argue way more versatile then. There’s always something to admire about a hungry artist who hasn’t made it big quite yet and they find their big brake. For Drake, in my opinion, it was this album.

My mom was riding her Odyssey, I was sitting in the front seat. For whatever reason, she asked for this song to be louder so she could dance along to it. She never dances, I never dance with her. We drove down Willow Road and got to share a moment together with some God awful dance moves without a care in the world.

My mom is one of the kindest souls you’ll meet. She always knows when something is wrong no matter how hard you hide it. She apologizes way too much. She calls all the time. I always answer.

Have a fantastic patty’s day!

Grown Up by Danny Brown

I mean, are you kidding? 70 degrees in Chicago on a Friday, college basketball on all day, St. Patrick’s day celebrations tomorrow. Stop it.

I don’t have much to write today other than a song I think fits today’s vibe perfectly.

We used to go bowling back in college during football camp. I had a teammate that drove a truck we all used to pile in back in the day. I would blare this song in the car on the way over.

As Mr. Brown said, we were rushing out of kids just to be grown up. Now that I’m somewhat grown (?) I look back on this song with a ton of great memories.

Since this song reminds me of college, on a day like this you’d be silly to even think about going to class in the afternoon. Grab some boys and go hit the links, go find a patio, go on a walk, do something. Enjoy some good music while you do it.

Tabula Rasa by Earl Sweatshirt

My first job out of college was selling HR software to car dealerships.

In other words, I would call on Doug Dimmadomes and try to pitch them on this software that would give them quality hires. I couldn’t speak the car language, it wasn’t really a great fit.

But I learned a lot. I had to make a ton of cold calls a day and got pretty solid at it. The best part of that job was the people.

I had an awesome manager and great colleagues with me in the pit. I remember us cold callers had to work the Saturday of St. Patricks day. I convinced a few of them to go in the office since our office overlooked the river getting dyed. We had a few daddy sodas well before noon as we ripped some coldies watching the swarm of green underneath us. A great memory with some old colleagues I don’t talk to anymore, but happy I share the memory.

I eventually got promoted a few months later. However at that time I got moved into a role I really wasn’t prepared for. Not only that, but we weren’t doing so hot either.

I remember in my last final weeks with the company I was so flustered – I couldn’t make a sale. I couldn’t hit water even if I fell out of a boat.

The day was ending and I played this song accidentally out of my computer when I thought my headphones were connected. One of my coworkers jokingly asked “setting the mood?” with the jazzy beat slipping through the speakers.

This is one of those beats where it doesn’t really make sense why it works, but it does. It’s kind of like a scary movie – you know it’s scary but want to keep watching for whatever reason.

Earl has been a favorite of mine for a while. He’s so profound with his lyricism, to a point where I can’t even dissect it. All I know is he’s been through hell and back and has rapped through it all, and I’ll appreciate him for that always.

Bounce by Flatbush Zombies

I just saw that this album came out yesterday 9 years ago today…

Man…

What a TIME. If you were around for the Flatbush wave, you get it. If not, you just had to be there. Sometimes I would watch this laced odyssey tour on youtube instead of coffee in the morning – both had the same affect.

There was a meme circulating around on twitter recently that was something along the lines of “name a song where you’d ask the producer how tf they made this beat”. Anytime this circles back to me, I always think of this song. I’d pay good money to see how Mr. Erik the Architect made this beautiful beat.

This song screams junior year of high school. It’s still in the rotation to this day.

I remember vividly we had Friday circuits in the off season for football workouts – the hardest day of the week. We just wrapped up a hard lift and headed for my friends car, Lana (a red volxwagen my friend named inspired by Lana Del Ray).

We hadn’t even left the parking lot when this song came on full blast and my friends all started blaring “YSL pants with the zippers…YIKES!!!” as we headed into the weekend.

If you need a little motivation to get over the hump on humpday, blast some bounce and lock in.

Birthday by Katy Perry

I saw an old friend/teammate of mine get engaged a few days ago. I wanted to give him a quick shoutout.

I was fortunate enough to be brought up to the varsity football team as a sophomore when I was in high school. At the time it was a big deal.

I’ll never forget my first team meeting with the big boys in the summer. I wore a grey nike long sleeve, nike elite basketball shorts, and some white long tights. I had to get something from the front of the classroom when one of the special teams coaches called out “hey, tights guy!” and it got some laughs from the seniors.

When you’re the youngest on the team you tend to get a lot of attention. Not only was I one of the youngest, but smallest too. The bell curve of nerves to excitement then down to fear was very real and fast in those first initial weeks.

My most humbling moment came when I was lifting with the team during my first week. If you’ve seen whiplash, I felt like I was Andrew when he got set up by Terence Fletcher at the end before going on his epic solo. A step too slow with weight way too heavy desperate to just fit in so no one realized how out of place I was. One of the seniors (who is now one of my closest friends) pulled me aside and said ~nicely~ I need to step it up.

I grew up fast – I didn’t really have a choice unless I wanted to be brought back down to JV.

I went back to what I knew best – just playing. I soon gained some respect from the seniors and started to fit in. They started to invite me to things, opened up a world for a kid who couldn’t even drive.

I knew I had made it when the seniors would start to offer me rides. When you’re a sophomore hanging out with seniors in high school, it’s the equivalent of knowing the guy that owns the nightclub, getting to skip the line and be apart of the show. It’s arguably one of the coolest things you could do at the time.

We were on our way to a 7on7 tournament – I rode in the back with two seniors. One was arguing how you need to listen to rap on the way to a game and country on the way back. There was a lot of back and fourth, and finally my teammate had had enough and played this Katy Perry song with no shame whatsoever.

It might be Katy Perry’s most underrated song arguably ever. Whenever I hear this, I’m brought back to the back of a beat up honda having to move a sea of spit cans with my legs with some super cool seniors just happy to be along for the ride.

For My People by Joey Bada$$

There are the Sunday scaries and the Monday spookies.

The Sunday scaries are like the day before the big game, except it’s not really a game, it’s life. That pit in your stomach, cold sweat, trying to run backwards on the time treadmill only to realize it’s going to come one way or another, so you might as well watch some white lotus and try to get some shut eye.

The Monday spookies is gameday. Sometimes it feels like an out of body experience. You’re signing into your laptop to start the day thinking about if you even had a weekend to begin with, and the cycle restarts.

But its 70 and sunny in Chicago people. I couldn’t have a bad Monday even if I wanted to.

---

I first heard this song right around this time a year ago on a walk on a Monday walk. Joey Bada$$ is such a talented artist, man. He made arguably one of the best mixtapes of all time at the ripe age of 17 YEARS OLD. Dude was rapping about lighting bongs and ripping thongs while I was keeping my hands at 10-2 taking my DMV test.

The jazzy beat and the synthesizer in the intro make me feel like I can take on anything that comes my way on a Monday. It’s a beautiful song amongst some great ones on the album.

Also, speaking of synthesizers, they remind me of one of my favorite shows, the Regular Show, when Gary and David have the synth battle up in synthos. I’ll never forget showing my friend a clip of the famous battle during our senior year of college before we had a silly Saturday.

Only the Bada$$ himself could make a song that would bring me back to a show I’m fond of and a memory of a simpler time. Enjoy the Monday, people. Get outside or pop on your favorite cartoon to get through the Monday spookies.

Blessings by Chance the Rapper

I was fortunate enough to have an academic advisor during my college days that eventually turned into my lifelong mentor, Dr. Bryan (he’s going to hate that I don’t call him Mark – I haven’t been able to make the switch just yet).

At my college, if you go in with a major undecided they randomly pair you with your advisor. I got partnered with Dr. Bryan in the theatre department. I knew I wasn’t going to be Leonardo DiCaprio anytime soon, so I figured I would meet him and then switch once the meeting was over.

I walked into his office and was instantly drawn to a Jordan 3 shoe on his shelf. He explained how his favorite Jordan design back in the day was the 3, but has moved over to SB’s in recent times and showed off his customs.

As a sneaker head myself, I felt like I was in a fever dream.

We spent a majority of our meeting discussing his Cubs hat. He grew up in Indiana but spent a fair amount of time in his 20’s right off Addison Ave. We reminisced about where we were during the 2016 game 7 world series – I went into great length about how one of my buddies proceeded to punch a wall in his own house out of excitement when Rizzo caught the final out.

From that meeting on, I never looked back about getting another advisor. I’m happy to share that we became great friends, and someone who I still reach out to to this day. He’s someone who has lived a thousand lives, taken a few trips around the sun, yet will make time even for the happy-go-lucky me’s of the world to share his two cents. A wise man beyond his years to say the least and still makes time to hit his 4:30 am runs.

Just a great mentor and friend – I’ll always be appreciative of you, Mark (there I said it).

---

ANYWAYS, he recommended a beam of light book during a time of despair in COVID of 2020 by Hanif Abdurraqib, who is now my favorite author, called They Can’t Kill Us Until They Kill Us.

The first chapter centers around Chance the Rapper’s Coloring Book Era. To me, this album sounds like he’s standing from his balcony on a Sunday afternoon looking out at Navy Pier. He sees the tabs of ACID in his peripherals, or whatever he’d use in his previous life to fill the void, and instead let the moment in itself fill the gap being his new source of inspiration. A truly authentic, rich album.

Hanif focus’s on his song Blessings. He goes on to explain how blessings are essentially a blip in time that lifts you above from what holds you underneath.

I couldn’t think of a better song for a better day. As we start to turn the page on the week, I think about all the blessings I’ve had just today. I was able to eat a bacon egg and cheese with one of my best friends at the park, find a new walk path, go to the produce section at the grocery store, and currently making dinner with the lads.

Whether it was adding another hour of sunlight to the day (shoutout CST) or taking a moment for yourself, I hope you all enjoy some blips of time that lift you above on this fine Sunday.

Over My Head by The Frey

My sister loves to facetime me before 9:00 am on the weekend with her kid when I’m…tired.

However I wasn’t tired this morning, so I decided that this would be a tribute to her (hi maggie).

---

I grew up with four siblings, three brothers and one sister.

Maggie is by far the best sister I have.

We are ten years apart, but you wouldn’t know that given how close we are. We shared a room when I was in 7th grade and she was her first year out of college. A match made in heaven.

It got to the point where I didn’t even set an alarm because I knew I would wake up to either her 10 snoozes or her Maroon 5 playing from the shower down the hall. My sports center sessions were often abruptly ended for The Real Housewives of Orange County. I unwillingly sacrificed Scott Van Pelt for Tamra and Gretchen often.

We shared another living stint my senior year of college when I got sent home for a semester during COVID (long story – I’ll explain another time).

It was right around this time where I got pretty big into Monopoly. Even though my brothers were involved, it always came down to Maggie and I fighting for Park Place and Broadway. If you want to test a true friendship or brotherhood, I suggest a game of Monopoly – if you can survive that without killing each other I think that’s a good bench mark.

---

ANYWAYS – The Frey! It was my senior year of high school, I had just stepped out of graduation (picture below) and was heading to dinner with my family and friends. Majority of my siblings were at the age where they could drive, but I elected to hop in the car with Maggie to take me to dinner. On the way over we rolled the windows down and let this song flood the car, singing word for word together the whole way without a care in the world.

And so whenever I hear this song, I think of my roommate, monopoly nemesis, sister. It reminds me of everything I appreciate about her. She has a unique way of saying the right thing at the right time. She never wants to miss a moment yet knows her boundaries. She has been there for me in my highest of highs and lowest of lows. I’ll always be grateful for Mags.

sidebar: i think this song encapsulates the mid 2000’s aesthetic perfectly – an era I know my sister just absolutely thrived in. It makes me think of all the great 2000’s shows, House being my favorite. Shoutout Greg House.

Have a fantastic Saturday people. Tell your sister you love her.