A bit tangential but closely related, I believe French HipHop / Rap makes such a good use of our language and all the slangs which I find lacking a bit in English HipHop.
I don't know if it's cultural or if I am really unaware of the equivalent in English, but it is such a delight to see the creativity of those folks.
"Toujours en déplacement le soir \ Mais, c'qui compte, c'est le dépassement de soi" > The play on déplacemment (being out of town) / dépassement (overcoming) ... le soir / de soi. Brilliant
I'm not sure if this is what you meant but there's a ton of word play in American Hip-Hop, it's pretty core to the genre. Literally any rapper you pick will be doing some amount of word play.
Sure I think MF DOOM is a good place to start especially his Madvillainy album with the producer Madlib which is really well regarded. More recent stuff I enjoy is Mick Jenkins from Chicago, his 2014 The Waters mixtape was also really well reviewed. Aesop Rock is also generally thought of as a really good technical rapper. His album None Shall Pass from the Def Jux days is really good though I prefer Skelethon which has less word play but is also brilliant.
I can't edit my original comment anymore but if you do have an interest in French, I strongly recommend studying the first 2 examples because they are pretty much full of those carefully crafted punchlines.
Relatedly, but further away from OP, and.not rap/hip hop, but Frandol's "l'un contre l'autre" makes a very good use of double entendre. https://m.youtube.com/watch?v=BNdxHUv3vmc
I don't know if it's cultural or if I am really unaware of the equivalent in English, but it is such a delight to see the creativity of those folks.
A few recent examples :
https://genius.com/15760906 < Cadillac | Game over : A song about death.
"J'écoute des CDs, des sons de l'au-delà" > I listen to records (CD), sounds from the other side. Des CDs also sound like being dead (décédé).
https://genius.com/Odezenne-tu-pu-du-cu-lyrics < Odezenne | Tu pu du cu
"T’es stupéfiant \ Je te roule, je te fume \ T’es stupéfait" > Word play on stupéfiant which is both a word for drugs and being surprising / stunning.
https://genius.com/Nekfeu-egerie-lyrics < Nekfeu | Egérie
"Toujours en déplacement le soir \ Mais, c'qui compte, c'est le dépassement de soi" > The play on déplacemment (being out of town) / dépassement (overcoming) ... le soir / de soi. Brilliant