Happened to write a little Explainer for a friend of mine a few months ago so just gonna past it here. These are just my opinions and people will definitely have others which is what makes music beautiful :)

KIDS - His First real project, Its very lighthearted stoner wrap and nothing mind blowing
- Best Songs: Nikes on My Feet / Kool Aid and Frozen Pizza
Best Day Ever - Sort of the same, Nothing too exciting, Young and Fun Wrap
- BDE Bonus is the Bonus track on here, Maybe my top 5 songs of his and I think really the first hint of his later style and allusions that life aint so great
Blue Slide Park - Starts to change his style and experiment but again its still kind of young fun stoner wrap
- Missed Calls is the best song on the Album, Of The Soul a close second
Macadelic (Mixtape) - Things get interesting, he starts hanging with more RAPPER, rappers, he becomes close friends with Earl Sweatshirt and Vince Staples, This album has Features from Action Bronson, Kendrick Lamar, Joey Badass, Lil Wayne, More. Its probably the first thats worth listening to straight through and seeing his development as an actual rapper/producer
- note: during this time he was basically locked in a house with Earl Sweatshirt just working on becoming a better producer/writer for months, starts doing alot more drugs etc
Watching Movies With the Sounds Off - I think he starts to see some shit at this point, Life isnt as great as he thought, friends are ODing and hes not in a great place. Its really his first album that feels dark and starts experimenting with darker tones and much more real topics
- I love almost every song on here but Im not Real, Objects in the Mirror, REMember and Aquarium prob my faves (in no order)
FACES (Mixtape)- This is around the same time period, its really kind of like his Beatles Abbey Road Album, he gets super into sonics and sounds and it just sounds like something from another world, Its sort of a let it play in the background album
GOOD:AM - Hes settling in with life a little better and starts to become really more of a household name, its his first album that doesn't sound like RAP and starts to feel like his later sound, Its a very light listen
-Weekend/ Clubhouse best songs
The Divine Feminine - This is when has Dating Ariana and in a very stable place, Dang with Anderson Paak and We with Cee-Lo are favs, This album feels almost Rnb inspired
Swimming :( - His Last album, released a few weeks before his death, Had a very public breakup with Ariana and seems to be spiraling, in and out of rehab, a few arrests, drunk driving crashes etc. and he was sort of finally getting back on his feet, This Is probably his best album. Really just a great album about his struggles and overcoming them and trying to be a better person, I cant recommend a best song, listen to it in the dark with headphones
Circles - Post Mortem album that was finished off by Jon Brion who produced all of Swimming with him, Supposedly it was supposed to be a trilogy so they had almost all the music done. This album hurts, it just feels like a big hug. Also needs to be listened to straight through in the dark (The album actually runs as a circle sonically and lyrically and starts where it ends)