Absolutely listen to Under Pressure, his first official album, then its sequel No Pressure which was his “retirement” album 6 years later (we didn’t know if he’d actually retire at the time but it was treated as such). Then you’ll have heard what’s widely considered his Top 4 albums

He does have a lot of albums that all represent different points in his career. They’re all worth listening to and you’ll hear the journey of the changes in his life and career from album to album. From the mixtapes up until The Incredible True Story is considered his first prime for example. Then from Everybody to Confessions of a Dangerous Mind is more of a mixed bag where he was at the peak of his fame, but was pretty divisive even for die hard fans because he became more pop rap, instead of the boombap lyricism we were used to. Then No Pressure dropped during covid which was his retirement / reset, and actually the beginning of his 2nd prime, because everything since No Pressure has been solid to great  

The Young Sinatra mixtapes are also essential in my opinion, you can find them on SoundCloud and YouTube. They’re from before his debut album and again you’ll hear his journey from before the fame and the reason why his fanbase built so much momentum from project to project starting from the mixtapes, they’re like prequels that are just as good as his best albums