I can give you like 100 lists and they'll all be wildly different. Sometimes my mood is more sad and depressing, other times I'm looking for stuff that's super high energy. It's really hard for me to compare a storytelling song like "Dance with the devil" to a song that's super hard and aggressive like "Set Trippin" by Casanova. Sometimes I care about a rapper's technical skill, but other times I just really like a song even if the artist isn't that great of a rapper. I think Casanova is a great example of someone who I don't think is a good rapper, but who made one of the best/hardest songs of all time. It's also hard to really compare a song I've listened to thousands of times since 2003 to a song that I just heard for the first time last month.
I'm just gonna go with the first 5 songs I can think of that I've listened to a lot, which I feel stick out as important to me for some reason. I'm also going to leave off any songs that I think most people know, e.g. Kanye's entire "College Dropout" album is probably the album I've played more than any other in history, but I assume most people know songs like "All Falls Down" and "Last Call"
I'm sticking to the theme of hip hop songs only. I might drop some more later
1. Royce Da 5'9 - Return of Malcolm. I was already a fan of Royce when this song came out, but this is the song that really elevated him to my #1 favorite rapper, and he still hasn't moved from that list. If anything, he's only created more separation between himself and everyone else.
NC is censoring part of the URL so I can't embed it. The mixtape version of this song uses a different beat, but this one is much better imo.
https://www.youtube.com/watch?v=p4EZoNlCA
then add "CA" to the end of the URL above
but here's a different, similar song from Royce which is arguably just as good, if not better. I just heard this later down the road and it only further cemented his place:
2. Little Brother ft. Elzhi - Hiding Place. I encourage people to check out the entire album, "The Minstrel Show". 9th wonder is an incredible producer, the songs are all super fire, but I really added this to my list because it was my first introduction to Elzhi. IMO Elzhi's feature on the verse is one of the best examples of a feature on a song stealing the show since AZ on "Lifes a bitch".
3. Atmosphere - The Pill. I think this song is the first song that really sort of made me more aware of the idea of "melodic" rap. Another great song that I almost listed in this same vein of melodic rapping non-stop while just dropping introspective thoughts is "Peanutbutter Waffles" by Ryan Caraveo.
4. Chino XL - Wordsmith. I'd like to think I would've listed this song regardless of whether Chino passed away. I used to listen to this song on repeat all throughout high school in addition to the entire "Rip The Jacker" album by Canibus. I was already into rap battling, so Chino was one of very few people at the time that took ideas like wordplay and punches and put them into their actual music. This song was for sure a huge influence on my writing at the time and has always been a phenomenal song to me, not only because it's lyrically impressive, but also because I feel like it's just a genuinely dope song
5. DZK - The Great Below. I'm hoping that we've gotten to the point in 2024 where it's not corny to list internet rappers. Tbh I had never heard the NIN version of this song, so I always thought the entire song was him singing. But this is still an incredible song that helped me therapeutically as a youth
One last mention, which is one of the examples of someone who is tbh not a very good rapper from a technical standpoint, but I actually like his music because if I'm feeling sad/depressed, it's something that I find to be relatable, introspective, and poetic.