1. “The Cut That Always Bleeds” 

“The Cut That Always Bleeds,” from Gray’s debut album “Kid Krow,” is a melodic masterpiece depicting the desire to leave a toxic relationship but not being strong enough to. Referring to it as “the most emo song on the album,” Gray mixes piano notes and gory lyrics to depict the harmonious clashing of his unrequited love. It’s easy to find yourself in the position of caring for someone who does not reciprocate. The devastating reality that you’ve given your all for someone else’s nothing seeps through the lyrics, putting all emotions on the table. 

2. “Memories” 

“Memories,” off of Gray’s second studio album “Superache,” encompasses what it’s like to deal with an ex-lover who somehow keeps coming back. In the song, Gray says he wishes his ex would just stay in his memories; it’s hard to get over someone when you keep seeing them around. The lyrics of this song are simply addicting and will be stuck in your head after you give it a listen. This song will have you screaming, “Curled in the fetal position / too busy playing the victim to be listening to me,” every time.

3. “Overdrive” 

Gray doesn’t make many upbeat songs, so of course, this one from “Superache” has to be in the top five. If “Overdrive” isn’t on your driving playlist, it definitely should be; it was made to be played while driving with the windows down and the wind blowing through your hair. The song is about diving into romance without thinking about the consequences or risks. The song encompasses a fun, carefree night with someone you have an instant connection with. In the midst of angsty breakup songs and ardent ballads, this one definitely stands out. 

4. “Winner” 

“Winner” is a catchy single off of Gray’s upcoming album “Found Angel,” which will be released April 5. This song is a heart-wrenching ode to familial abandonment by a narcissistic parent, shedding light on the different type of heartbreak that comes with being hurt by someone who will never admit they’re wrong. The lyrics “There’s nothing / That ever did quite kill me / More than what you did / Now you really are the winner” will hit every single time. There is something cathartic about giving the person who hurt you one last trophy. 

5. “Lookalike” 

At the end of the day, this song off of “Sunset Season,” Gray’s first EP, will always be one of my all-time favorites. “Lookalike” is one of the two non-singles on this EP, and it seamlessly portrays allegorical songwriting, with the theme of doppelgangers driving the metaphoric lyrics. The song about an ex-lover now being with someone who looks oddly like you is silly yet intelligent and witty. Gray suggests that his past partner will always find him in new romances. My favorite lyric is “Can’t compete, ‘cause I’ve already won.”