From Wale’s Growth to a Sister’s Recommendation
From artists finding new ways to open up to music discovered through his sister, Taylor’s picks reflect a listener who values vulnerability, connection, and the memories songs create.
Taylor approaches music through the people and experiences that give it meaning. He’s drawn to artists who are willing to be vulnerable about where they are in life, but some of his favorite discoveries have also come from the people closest to him. Across his answers, music becomes something shared as much as something listened to, whether it’s an artist he has watched evolve or a new favorite introduced by his sister.
The August 10 to 12 prompts offer a closer look at the different ways Taylor connects with music. The first starts with the idea of humor in album covers and considers how something as simple as an image can say a lot about the artist behind it, while also taking on a life of its own once people start talking about it. From there, a current hip-hop favorite becomes an opportunity to talk about the feeling of overthinking and why hearing an artist put those thoughts into words can make a song hit differently. The final prompt turns to an artist he didn’t discover on his own, and the answer traces how a recommendation from his sister eventually became something much more personal.
What’s an album cover you think has a sense of humor?
The first and only answer that came to my mind was Certified Lover Boy by Drake. When Drake announced Certified Lover Boy, I expected the cover to be something more along the lines of Take Care, with a more traditional and emotional aesthetic. Drake really threw the world for a loop when he did the most Drake thing possible and revealed the album cover featuring nothing but a grid of 12 pregnant woman emojis. To me, the humor comes from how unconventional the cover really is and the widespread reactions and jokes it inspired online after it was revealed.
This cover is a perfect representation of Drake’s personality and how he has presented himself throughout his career. Throughout Drake’s discography, he has provided us with many different yet memorable album covers that can be seen as bold and risky, and Certified Lover Boy follows that same trend. I am pretty sure myself and many others had the same thought when seeing the cover for the first time: “I could have made that same album cover.” The cover did its job of getting everyone talking, but I feel like the record became more memorable because of its humorous cover than the music itself. I do not think that was Drake’s intention, which is unfortunate because there are some great tracks on the album that deserve attention. Overall, I think this cover stands out because Drake took something as simple as 12 emojis and turned it into something people still remember and talk about years later.
Which hip-hop song are you currently vibing to?
The recent release of “Overthink” by Wale featuring Elmiene couldn’t have come at a better time, and it’s been on repeat for me ever since it dropped. After hearing everything is a lot., I believe “Overthink” continues to show Wale’s growth, especially in the way he’s become more willing to open up and be vulnerable in his music. Wale does a great job showing that he doesn’t have all the answers, and I think that’s what makes the song feel so relatable. He taps into those moments where you find yourself second-guessing things and overthinking your emotions or relationships. That honesty is what really connected with me.
What really makes the song click for me is Wale’s writing. He captures the anxiety that comes with overthinking in a way that feels honest and familiar, putting words to the constant second-guessing that many of us experience. I often find myself cycling through thoughts in my own head, sometimes at a pace that reminds me of Wale’s delivery on this song. I think that’s what makes “Overthink” hit so hard—it captures those conversations we have internally that aren’t always easy to put into words or express out loud. Wale’s writing does a great job of bringing those thoughts to life, while Elmiene’s softer delivery feels like the emotional side of those conversations we usually keep to ourselves.
Together, Wale and Elmiene create a song that feels deeply personal while still being something so many people can relate to. “Overthink” has been the hip-hop song I’ve kept on repeat since its release because of its relatability and honesty.
Which artist is easily becoming one of your favorites?
I’ve always enjoyed having a wide variety of artists and genres to listen to because there is always something new to discover, and over the last year, Alex Warren has become one of the artists I keep coming back to. What makes Alex Warren’s addition to my playlist different from many other artists is that I didn’t discover him on my own; my sister was actually the one who introduced me to his music. She encouraged me to give his music a listen because she thought it could be something I would end up enjoying. From the first listen, I was drawn to the emotion behind his music and the personal subjects he wrote about, which felt different from the other artists and songs I usually listen to.
I found his music to be very personal and intimate, which is something I look for during the heavier moments in my life. I felt especially drawn to songs like “Burning Down,” which focuses on Alex walking away from a toxic friendship, and “First Time On Earth,” which explores themes of trauma, forgiveness, and understanding that everyone has their imperfections and is still trying to find their way. I appreciate artists who are able to tell stories through their music and create songs that listeners can connect with on a deeper level, and I feel that Alex Warren does exactly that. A song I relate to closely is “Troubled Waters,” as it explores his fear of being abandoned by the people he loved and how that fear led him to push others away. Seeing him express those experiences through music is what makes his songs feel so honest and relatable to me.
Not only have I been able to enjoy his music through streaming, but over the last year, I’ve also had the chance to see him perform live twice, both times alongside my sister. So, it’s not only the way his music has made me feel, but also the memories I’ve been able to make through his music that have made him one of my favorite artists.
Taylor describes music as connection almost immediately. He talks about wanting to understand himself a little better through what he listens to, but also about the people and artists that give those songs more meaning. He’s especially drawn to honesty and vulnerability, which comes through in the way he talks about Wale’s music and the artists he’s continued to explore. There’s a genuine interest in what people are trying to say, not just how the finished song sounds.
That openness probably explains why his listening can move so easily from something someone else recommends to an artist he ends up following closely. His sister introduced him to Alex Warren, and over the last year that discovery has turned into two concerts together. Then there’s Giveon, whose Give or Take Tour was Taylor’s first concert back in 2022. He still remembers hearing “This Will Do” with the live band, years later. Some songs just pick up those associations without you really planning for them.
He also seems to know what he wants from music, even with all that room for discovery. It has to feel genuine. It has to give him something to think about or recognize in himself. And sometimes, it’s enough for a song to simply become part of a good memory. His taste may keep changing, but those things seem to stick around.
A record collector, movie enthusiast, sports fanatic, and concertgoer with a deep appreciation for music and an appreciation for the authentic moments that make it meaningful.
