My Gregory Dillon Song Countdown
Since his arrival on the queer music scene in 2018, Gregory Dillon has amassed one of the best and most consistent body of singles that I can think of. Single for single Gregory always delivers the goods and he hasn't made one mis-step thus far. Gregory's music is usually heavy on atmosphere with strong hooks, detailed production and soulful vocals. Gregory mixes music of different eras from 80s synth pop through 2010's chillwave, which gives his music a feeling of timelessness while still feeling current and fresh.
One of my absolute favorite aspects of Gregory's music is how transportive it feels. As a queer kid growing up in the closet I turned to music for solace as well as an escape from a world not built for me. It's why some of my favorite music transported me to different worlds and places. For example this is why the Beatles psychedelic era is my favorite for that group and why I can really get into atmospheric music like Shoegaze or Chillwave when the feeling hits. Still most of that music didn't speak directly to me as a young gay boy but Gregory's music really does. Gregory's music is transportive with a heavy emphasis on escaping to different to places where he can be happy and feel accepted as a queer person. So Gregory's music not only reminds me of other music I love but it speaks to me in a way no music before queer music ever has, which is why I connect so deeply to him as an artist. His music reminds me of the days when I was in the closet as a teen living in suburbia and feeling all alone with only music and my own fantasies to keep me company.
So now I present a countdown of all 12 Gregory Dillons songs. For this countdown I focused solely on his own material that he wrote. I'm not including any of his cover songs or remixes here. Also like I said for my Michael Medrano countdown I love every song on here. Every song here is an A if not an A+ so even if one of your favorite songs ranks low just know that I do love that song and when you do a song countdown something has to be at the bottom. Nonetheless all 12 of these songs have been in constant rotation for me since they were all released. I have not gotten tired of these songs yet and I don't think I ever will either. So with that said let's jump into this countdown.
12. Vacuum (2019)
As those who follow this blog know, I covered Vacuum back when it was first released in the fall of 2019, which seems like a lifetime ago in this post pandemic world we live in. At the time my thoughts were that this song marked a new direction for Gregory and I still feel that way. Up until that point his singles were atmospheric but uplifting. Vacuum was much darker lyrically and musically, but I think this change in direction still worked and opened up the possibilities of what Gregory could do as an artist. Vacuum also reminded me of Depeche Mode's leather era and this song could have easily fit onto their Violator album from 1990. Despite being at the bottom of this list I still think highly of Vacuum and I still listen to it regularly almost 3 years later.
11. Lovely (2020)
Lovely feels like the spiritual sequel to Vacuum since it's the first darker song Gregory had released since Vacuum. That said, you can hear how the production has jumped up a few notches and the chorus sticks just a little bit better too, which is why it's ahead of Vacuum. Again this song shows off Gregory's versatility as an artist and I'm glad it exists. That said, maybe the reason these 2 songs are at the bottom is because I like when Gregory is a little more uplifting and fun. Still that's such a minor quibble at best because again I still listen to this song all the time and I still think it's brilliant.
10. Sad Magic (2020)
The title track to Gregory's 2020 sets the tone perfectly. The song, much like the EP itself, is drenched in nostalgia for growing up in the suburbs while still dreaming of escaping the suburbs in order to find your true self (aka coming out of the closet). The song is a mixture of 80s synth pop with bits of Chillwave thrown in to keep things even more interesting. While Gregory's songs have always been great right from the start I can hear how his production and songwriting has subtly improved over the last few years and that growth is very evident on Sad Magic. As Gregory says it's a bop you can dance to while crying at the same time. I think that perfectly sums up the Gregory Dillon brand.
9. Mischief (2020)
Mischief was not Gregory's first collaboration per se, but it's the first duet he has done as far as I know. Zach and Gregory make for a very fun pairing here and it was interesting for me to learn on my various livestreams with both of them just how different they are when it comes to the act of Mischief itself. Gregory isn't above doing some serious mischief when the opportunity presents itself, whereas Zach is way too timid to ever break the rules or go against his parents wishes when he was younger. In a way that reminds me of my husband and me because my hubby is the mischievous one and I follow all the rules to a T. The song itself definitely feels more Zach Benson as it doesn't have the heavy atmosphere of Gregory's songs. Instead it's just a feel good bop with traces of Daft Punk's One More Night in its DNA, which I know is a fact because every time I see Zach perform this song live he sings a medley of Mischief and One More Time on stage.
8. Painted Blue (2018)
Gregory's second single was my introduction to him in the early weeks of 2019. It grabbed me immediately which doesn't always happen with new music by a new artist I've never heard of before. Still that production and that voice jumped out of my tiny phone speaker so much it could not be easily ignored. This song feels very ethereal and starry to me as if I'm flying through the stars as I listen to it. Lyrically the song is a bit more grounded as it details the end of a relationship that Gregory can't face right now.
"We used to dance within the flames
Making love all night right into the day
But now we face the cold
I try to stall from heading home
'Cause I’m way to0 scared to let you go
And feel alone again
[Chorus]
Crying is hard, deepening the pain still
Dear God, feel I lost an angel
I can’t bare to look back at you
Crying is hard, deepening the pain still
Dear God, feel I lost an angel
This sad boy is painted blue"
Even without knowing these lyrics you can still feel the emotion pouring out of Gregory thanks in large part to his amazing vocals. It was a great introduction for me to Gregory and every time I listen to Painted Blue I can still remember how it felt hearing it for the first time.
7. Love Again (2019)
Love Again was Gregory's 4th single and in some ways it felt his most overt pop song up till that point. Now his first 3 songs were pop songs, but they were all drenched in heavy atmosphere, which I loved, but here he pulls back a bit on the atmosphere. This slight change made all the difference, because I remember more people really starting to like him around this time. The lyrics were also a bit more grounded too, which I think helped it appeal to more people. Unlike Painted Blue, where Gregory is lamenting the end of a relationship, Love Again sees Gregory in those first throes of passion when new love feels exciting and electric:
"Lavender lightning
Tracing my fingers over you
Oh as you hold me
Kinetic potential starts to bloom
Drifting electric afternoon
Ready the feeling
I can wait for you and if you want me too
Steady the feeling
Just say you want me too
I wanna love again, wanna love again, wanna love again with you"
Love Again captures that feeling anyone who has ever been in love or had a huge crush can relate too.
6. Where We're Going (2019)
Where We're Going was Gregory's 5th single and I feel like it's the song that truly solidified Gregory being one of my very favorite queer artists at the moment. When I first heard the song during the summer of 2019 I picked up on the Chillwave influences very quickly, especially because in the years leading up to queer pop I was bing listening to a lot of Shoegaze & Chillwave music. I could hear acts like Washed Out and Small Black in the production of Where We're Going and when I told Gregory this he told me he loves Washed Out and Small Black. It was not only validating to hear I was correct, but that he was into music that I was very into as well. The music video was also super cute as Gregory's videos typically are and showed a little same sex affection in it, which is always appreciated.
5. Screenshots (2020)
First off let me just say that Screenshots is one of the best bops Gregory has put out. I remember when the song was being teased on social media and being instantly drawn to just how danceable it was. Lyrically the song touches upon crushes in the age of smartphones and social media and how you can pine for someone from a distance as you look over all their photos and messages over and over again:
"Babe, call me back
Been looking through the pictures we snapped, oh
I’m reading every message we had
Jus feeling reckless, replaying all the
Screenshots from the past"
This brings me back to my college days when I would have a crush on a boy and I would look over their social media pages constantly and hope they would message me back. As has become common for Gregory at this point the music video was good campy fun and it might honestly be my favorite music video of his. As Gregory said on social media he was living his own 60s desperate housewife fantasies in this extremely stylish looking apartment that apparently he only had access to for a few short hours. They obviously maximized the little time they had because it's a great video overall.
4. Plastic Ferrari (2020)
As we enter the top 4 I've noticed that the songs I've chosen for Gregory Dillon are the ones that really focus on that idea of escape, but through a queer lense, which makes it transportive in a way I've never really heard before. Plastic Ferrari was a collaboration with Yavin, who didn't sing on it but did help write it (Gregory would return the favor on Yavin's 2021 single Handsy). Gregory & Yavin both said the song's concept sprang from them talking about Barbie dolls and Ken dolls and they wondered what would happen if Ken admitted he was gay and ran off with another male doll instead of Barbie.
Now this is an extremely queer idea, especially for little gay boys growing up who want to play with Barbie dolls but are told no. I know as a young gay kid I wanted to play with dolls and My Little Ponies instead of GI Joe. Yet, I remember being shamed for that pretty early on and pretty often from peers, especially as I got older. Eventually I made the transition to action figures for superheros and Mortal Kombat, but I would always try to get the girl action figures so I'd have some female characters to play with. I also remember in my last days of playing with action figures I would sometimes set up two of the males to be in a romantic relationship with one another though I would never do that when my friends were around.
What's so brilliant about this song is that it's a story about Barbie & Ken that flips the script and makes Ken gay and then gives him this happily ever with another male doll. Queer people are not used to seeing ourselves in mainstream narratives and when we are it's usually much more tragic and sad. Yet, by going back to childhood toys and giving it a gay happy ending Gregory gave us something we all dreamed about as young gay boys, but that we never thought would ever happen. Plastic Ferarri normalizes playing with Barbie and Ken dolls for gay boys and then it gives us the happy ending we are so often denied. I think there is something so healing about that for me as a listener and others as well and I have to think it was healing for Gregory and Yavin too. Oh and the song's a bop but by this point you already knew that right.
3. Alien Boyfriend (2019)
Continuing on the theme of escapism in pop music through a queer lens we now have one of Gregory's signature songs Alien Boyfriend. When talking about this song Gregory said the inspiration came when he was much younger and felt more alone and he would dream about being taken to other worlds where he would be accepted for who he is and not for what others wanted him to be. Once again I relate to his story deeply, because I too had a lot of these same fantasies growing up as a gay kid in the closet who couldn't relate to any of my peers. I too wished I could escape this world and go some place where I wouldn't be judge for being gay or too girly. The song itself is atmospheric like Gregory's previous 2 singles had been, but it was much more a bop this time too, which made it sound even more soaring and life affirming, especially when it gets to the chorus and he sings:
"Feel my makeshift heartbeat
Violet high beams in your eye
Be my alien boyfriend
Racing through the night
Send me constellations
Worn out duffle packin’ light
Lost in deep translation
Meet me in the sky"
I can picture this entire scene that Gregory is singing about inside my head and when his voice really soars towards the end it can still give me goosebumps. In a lot of ways I think of this as Gregory's signature song because it gets to the heart of what makes him so great and what I love about him and his music. The video on the other hand was much more lighthearted and fun and it's a great showcase for Gregory's sense of humor. You can tell Gregory takes his music seriously but he doesn't take himself too seriously. Gregory isn't afraid to look goofy, which ends up making him even more endearing in my eyes.
2. Alone With You (2018)
Right out of the gate Gregory Dillon put his best foot forward on his debut single, which established his sound and vibe perfectly. Alone with You at first sounds like it's a love song about a girl but Gregory told me that it's actually about the moon particularly when it's late at night and all you have for company is the moon. The song already felt awe inspiring, but knowing what it's about makes the song sound even more perfect. I never get tired of this song and it still gives me chills every time I listen to it. It's currently my 5th most streamed ever on Spotify. Gregory Dillon knew what kind of artist he wanted to right from the start and as a result this great song represents the beginning of a great run of singles that is nearly unmatched in modern pop music outside a select few.
1. Sunset (2020)
As much as I love Alone With You I have to once again admit that Gregory got better as he went along, especially when it comes to production. That's why the song closer to his Sad Magic EP takes the #1 slot. Like Alone With You, which dealt with the awe inspiring beauty of the moon, Sunset of course deals with the awe inspiring beauty of a gorgeous sunset except the production here feels bigger and more epic. It sounds like a widescreen movie and every time that production ramps up for the chorus I get an endorphin rush. I've been listening to this song non stop since it was released to the point that it remains on my On Repeat playlist a year & a half later. I told Gregory that if I ever got a chance to see him live I would be in the front row singing along to every word of Sunset back to him. Well I did get to see Gregory Dillon live over the fall of 2021 and I did sing every word of Sunset back to him on stage and it was magical! It was a perfect moment of pop bliss and that's why Sunset is my favorite song by Gregory Dillon.
