Bot Dylan, or, adventures in the music taste of old white guys
2025-08-21
This summer adventure requires a bit of context. It started with two of my friends-- their names start with S and G so we'll call them Simon and Garfunkel because it seems relevant. They live together and (besides Formula 1) one of their main pastimes is torturing our other friend, whose name starts with L so we'll call them Led Zeppelin. Despite growing up here in Toronto, Led doesn't know the first thing about pop culture, and Simon and Garfunkel like to assign them things to read/listen to/watch so Led can get caught up on the past 50 years of media. One day Garfunkel figured out that Led couldn't name any of the Beatles, and to say this came as a shock was an understatement. Simon and Garfunkel were so determined to improve Led's music education that they set Led and the rest of their friends a challenge: during the summer of 2025, listen to all of Rolling Stone magazine's 500 Best Songs of All Time.
The following day, we were all invited to an intricately planned Discord server called The Citadel with a custom logo, a bespoke PDF of rules and regulations, and some incredibly cryptic terminology. I still don't know the story behind some of it, but given that it was mostly constructed at 3am, I don't think anyone does.
2025-08-21
This summer adventure requires a bit of context. It started with two of my friends-- their names start with S and G so we'll call them Simon and Garfunkel because it seems relevant. They live together and (besides Formula 1) one of their main pastimes is torturing our other friend, whose name starts with L so we'll call them Led Zeppelin. Despite growing up here in Toronto, Led doesn't know the first thing about pop culture, and Simon and Garfunkel like to assign them things to read/listen to/watch so Led can get caught up on the past 50 years of media. One day Garfunkel figured out that Led couldn't name any of the Beatles, and to say this came as a shock was an understatement. Simon and Garfunkel were so determined to improve Led's music education that they set Led and the rest of their friends a challenge: during the summer of 2025, listen to all of Rolling Stone magazine's 500 Best Songs of All Time.
The following day, we were all invited to an intricately planned Discord server called The Citadel with a custom logo, a bespoke PDF of rules and regulations, and some incredibly cryptic terminology. I still don't know the story behind some of it, but given that it was mostly constructed at 3am, I don't think anyone does.
The Discord message we all woke up to. Note the time: nearly four AM.
The rules. I guess we would have lost access to the challenge if we didn't do some of this stuff.
Alright, so in layman's terms, the challenge was this:
Every day Garfunkel would pick five songs at random (five songs made up a Covenant) from the Rolling Stone list. We would have to listen to all of them within 24 hours, as well as fill out a google doc with numerical ratings in various categories, album covers, reviews, and the most important part: rank out of 500. We had to rank each song on the spot, and (as far as I could tell) wouldn't be allowed to change our ratings, so we had to curate our preferences very wisely.
You might be able to tell from some of my word choices that the Covenants did not quite go as planned. I guess filling out an admittedly badly formatted google doc was a bit too much for busy university students. Three people filled out the first day's google doc: me, Led, and one other friend of ours. Simon and Garfunkel did not. Led quit the challenge after two days, and many of the people originally invited to the server hadn't even started. Meanwhile, I was dutifully fulfilling the code laid out for me in the PDF. As you might be able to tell, Simon and Garfunkel are nothing if not committed to the bit, and they would have no problem "culling" people from the challenge. But it soon became clear that they were going to have their work cut out for them if they wanted anyone to do the challenge at all. No other mention of culling was ever made, and although Garfunkel continued to post each day's covenants, the server was largely inactive after the first week.
But I enjoyed the challenge. The first song I listened to was "Kill Bill" by SZA, which is an absolute banger and I hummed it for a week. I would look forward to the daily covenant all day, and then put on my headphones for optimal listening quality. I ditched the google docs for a spreadsheet pretty quickly, but other than that, I followed Simon and Garfunkel's instructions to the letter. After a few weeks, Garfunkel's covenants grew more sporadic, before stopping altogether about a month in, and I missed them. I decided that, dammit, I was going to listen to all 500 songs before the end of the summer no matter what. And that's where Bot Dylan came in.
After obtaining the necessary server permissions from Garfunkel, I built a Discord bot (Bot Dylan) to message five songs from the list every day. I'd already surrendered my student ID to the Salesforce gods for a Heroku student account, so deploying Bot Dylan on Heroku was quite easy. A couple days in I realized I forgot to attach the database, but other than that it was smooth sailing. And ever since then, I've been listening to five songs a day (okay, maybe ten every two days, it's not as exciting as it used to be). At one point my dad decided he wanted to join the challenge, so I made a new Discord server (and new Discord account) for him, but after a few weeks he dropped out too. Thankfully, he dropped out before Bot Dylan made his programmed Cybersmith joke. That would have been awkward to explain.
Every day Garfunkel would pick five songs at random (five songs made up a Covenant) from the Rolling Stone list. We would have to listen to all of them within 24 hours, as well as fill out a google doc with numerical ratings in various categories, album covers, reviews, and the most important part: rank out of 500. We had to rank each song on the spot, and (as far as I could tell) wouldn't be allowed to change our ratings, so we had to curate our preferences very wisely.
You might be able to tell from some of my word choices that the Covenants did not quite go as planned. I guess filling out an admittedly badly formatted google doc was a bit too much for busy university students. Three people filled out the first day's google doc: me, Led, and one other friend of ours. Simon and Garfunkel did not. Led quit the challenge after two days, and many of the people originally invited to the server hadn't even started. Meanwhile, I was dutifully fulfilling the code laid out for me in the PDF. As you might be able to tell, Simon and Garfunkel are nothing if not committed to the bit, and they would have no problem "culling" people from the challenge. But it soon became clear that they were going to have their work cut out for them if they wanted anyone to do the challenge at all. No other mention of culling was ever made, and although Garfunkel continued to post each day's covenants, the server was largely inactive after the first week.
But I enjoyed the challenge. The first song I listened to was "Kill Bill" by SZA, which is an absolute banger and I hummed it for a week. I would look forward to the daily covenant all day, and then put on my headphones for optimal listening quality. I ditched the google docs for a spreadsheet pretty quickly, but other than that, I followed Simon and Garfunkel's instructions to the letter. After a few weeks, Garfunkel's covenants grew more sporadic, before stopping altogether about a month in, and I missed them. I decided that, dammit, I was going to listen to all 500 songs before the end of the summer no matter what. And that's where Bot Dylan came in.
After obtaining the necessary server permissions from Garfunkel, I built a Discord bot (Bot Dylan) to message five songs from the list every day. I'd already surrendered my student ID to the Salesforce gods for a Heroku student account, so deploying Bot Dylan on Heroku was quite easy. A couple days in I realized I forgot to attach the database, but other than that it was smooth sailing. And ever since then, I've been listening to five songs a day (okay, maybe ten every two days, it's not as exciting as it used to be). At one point my dad decided he wanted to join the challenge, so I made a new Discord server (and new Discord account) for him, but after a few weeks he dropped out too. Thankfully, he dropped out before Bot Dylan made his programmed Cybersmith joke. That would have been awkward to explain.
I got bored typing out all the songs. The idiots at Rolling Stone didn't put them all into a nice spreadsheet for me.
So finally, we come to the actual purpose of this blog post: the best reviews I wrote during four months of Bot Dylan-curated songs. Reviews are vibes-based only with some actual commentary on the music as an added bonus. I did a pretty good job ranking everything on the spot, but around early August I did have to start moving stuff around. That means the rank shown here might not be the original rank I gave the song, but it's within five or so ranks of the original.
Sexual Healing by Marvin Gaye
This man was born to write a soul adaptation of cbat.
Rank: 158
Dream On by Aerosmith
Classic rock is very hit or miss for me. This is a hit. I'm feeling very white today I guess. Maybe it's my sunburn peeling
Rank: 60
Bo Diddley by Bo Diddley
Whenever I hear about bo diddley I think of this bob dylan song where he references bo diddley but his voice is weird so it sounds like he's saying bob dylan so I always thought he was referring to himself. this song is meh
Rank: 364
I'm So Lonesome I Could Cry by Hank Williams
on the album Moanin The Blues
Wow he really is Moanin The Blues. I almost feel like I've walked in on an intimate moment with the blues
Rank: 410
That'll Be The Day by Buddy Holly
a solid song to nod your head to. maybe respectably in a public place. Although I can't think of a public place that would play music this old except maybe a ski lodge playing warren miller montages of people falling off lifts. I would fall off a lift to this
Rank: 362
Heartbreak Hotel by Elvis Presley
We get it, they're lonely. I'd rather go to hotel california. At least if I could never leave, I would never have to listen to Elvis
Rank: 435
The Message by Grandmaster Flash and the Furious Five
Old rap is so interesting cause it sounds like an orchestra of star wars robots set to the most tragic lyrics. *Can* this guy say the f slur? this song is a bit longer than it needs to be, attention spans aren't what they were back then
Rank: 349
Beat It by Michael Jackson
intro is giving denis villeneuve dune meets david lynch dune in the ABSOLUTE BEST WAY. i'm imagining kyle maclachlan next to parasol hawat
Rank: 36
Free Fallin' by Tom Petty
I usually never mention the album covers but I have to in this case because it is the pansexual flag for some reason. good for tom I guess. I grew up listening to this song on the "easy listening" station and I always thought the girl was "crazy about elves" instead of elvis and I just figured she was a tolkien nerd
Rank: 230
Visions of Johanna by Bob Dylan
Not sure I've ever heard a love-related bob dylan song, luckily it still has plenty of unrelated rambling about trains
Rank: 179
Won't Get Fooled Again by The Who
Famously covered by George W. Bush
Rank: 265
Heavy Metal Drummer by Wilco
finally I get to find out what is so good about this band that some dutch cyclist's parents decided to name their son after the band. so far it isn't anything to name your son after ngl
Rank: 293
Gloria by Them
smh woke has gone too far, even the bands have pronouns
Rank: 403
All The Young Dudes by Mott the Hoople
this guy sounds like if freddie mercury was a stoner and bad at singing
Rank: 239
Mannish Boy by Muddy Waters
Electric blues is a pretty cool genre, but I'd be curious to hear the reverse: acoustic folksy headbangers
Rank: 286
Paid in Full by Eric B. & Rakim
I definitely did not expect an actual financial conversation over a beat and that's kind of awesome they should have said their social security members. fish which is my favourite dish. WAIT THEY LITERALLY JUST LEAVE CAUSE IT TOOK THEM TOO LONG TO RECORD THE ALBUM LMFAOOOOO OLD RAP >>>>>>>>>>>>>
Rank: 137
Yesterday by The Beatles
Well, it's not Coldplay. It's not Fix You.
Rank: 6
Sexual Healing by Marvin Gaye
This man was born to write a soul adaptation of cbat.
Rank: 158
Dream On by Aerosmith
Classic rock is very hit or miss for me. This is a hit. I'm feeling very white today I guess. Maybe it's my sunburn peeling
Rank: 60
Bo Diddley by Bo Diddley
Whenever I hear about bo diddley I think of this bob dylan song where he references bo diddley but his voice is weird so it sounds like he's saying bob dylan so I always thought he was referring to himself. this song is meh
Rank: 364
I'm So Lonesome I Could Cry by Hank Williams
on the album Moanin The Blues
Wow he really is Moanin The Blues. I almost feel like I've walked in on an intimate moment with the blues
Rank: 410
That'll Be The Day by Buddy Holly
a solid song to nod your head to. maybe respectably in a public place. Although I can't think of a public place that would play music this old except maybe a ski lodge playing warren miller montages of people falling off lifts. I would fall off a lift to this
Rank: 362
Heartbreak Hotel by Elvis Presley
We get it, they're lonely. I'd rather go to hotel california. At least if I could never leave, I would never have to listen to Elvis
Rank: 435
The Message by Grandmaster Flash and the Furious Five
Old rap is so interesting cause it sounds like an orchestra of star wars robots set to the most tragic lyrics. *Can* this guy say the f slur? this song is a bit longer than it needs to be, attention spans aren't what they were back then
Rank: 349
Beat It by Michael Jackson
intro is giving denis villeneuve dune meets david lynch dune in the ABSOLUTE BEST WAY. i'm imagining kyle maclachlan next to parasol hawat
Rank: 36
Free Fallin' by Tom Petty
I usually never mention the album covers but I have to in this case because it is the pansexual flag for some reason. good for tom I guess. I grew up listening to this song on the "easy listening" station and I always thought the girl was "crazy about elves" instead of elvis and I just figured she was a tolkien nerd
Rank: 230
Visions of Johanna by Bob Dylan
Not sure I've ever heard a love-related bob dylan song, luckily it still has plenty of unrelated rambling about trains
Rank: 179
Won't Get Fooled Again by The Who
Famously covered by George W. Bush
Rank: 265
Heavy Metal Drummer by Wilco
finally I get to find out what is so good about this band that some dutch cyclist's parents decided to name their son after the band. so far it isn't anything to name your son after ngl
Rank: 293
Gloria by Them
smh woke has gone too far, even the bands have pronouns
Rank: 403
All The Young Dudes by Mott the Hoople
this guy sounds like if freddie mercury was a stoner and bad at singing
Rank: 239
Mannish Boy by Muddy Waters
Electric blues is a pretty cool genre, but I'd be curious to hear the reverse: acoustic folksy headbangers
Rank: 286
Paid in Full by Eric B. & Rakim
I definitely did not expect an actual financial conversation over a beat and that's kind of awesome they should have said their social security members. fish which is my favourite dish. WAIT THEY LITERALLY JUST LEAVE CAUSE IT TOOK THEM TOO LONG TO RECORD THE ALBUM LMFAOOOOO OLD RAP >>>>>>>>>>>>>
Rank: 137
Yesterday by The Beatles
Well, it's not Coldplay. It's not Fix You.
Rank: 6