I hope ppl won't judge me for this bc I've seen many older folks on here making fun of music like this in some comments, but he's like one of my favorite artists for tripping. I've actually discovered him when tripping for the first time and he's been part of every trip since. Cloudrap is like really experimental and his texts often don't hold that much meaning, and are rather another instrument that takes part in the songs. Especially when smoking weed and getting crazy closed eye visuals, I find becoming one with his songs so extremely freeing. He got so many different songs, so some might not feel that nice but here's the ones that have lead to amazing trips(I'll mark my absolute favorites with [!]):

Letting it all go[!]; Leanworld[!]; Starz[!]; Yoshi City; Fire; Eye Contact; Stars Align; Yellowman[!]; Dance in the Dark[!]; Acid at 7/11; Put me in a Spell[!]; Kyoto; Paradise Lost; Waterfall; Nobody Else[!];

If you want to try a whole album at once, I'd recommend starting with Starz as it's the most psychedelic sounding imo!

Edit: aaaa I had a typo in the title due to auto correct ☹️