Not sure if he has a compelling enough story, or creativity to really push himself more. He has told his come up. He has rapped about his current life. Someone like Jay felt pretty creatively stalled after The Blueprint 2/The Black Album, Kingdom Come was an attempt to break out, and only kinda worked.
Nas is just someone who is a little more weird and dark, and pushed himself into creative zones, with his own life and imagination. Someone like Pac just led that wild of a life, where his real life was spilling so much into the music, the content just kept coming. If he lived, who knows where he would have ended up? Every artist with 10 or 20 years in, is going to hit rough spots. Nas with HHID. Jay with Kingdom Come, and those came roughly 10-12 years into their careers.
Drake just isn't that person, and raps his own life, but he also doesn't lead with depth or vulnerability anymore. What felt deeper and more vulnerable in 2011, isn't anymore. It's like Jay with the drug talk. He got a lot of criticism for that. Still does. He leads with kind of resentment and chip on his shoulder. Sounds like Jay on The Blueprint 2, ironically.
Wayne to me, lost that battle 15 years ago, and never matured. Hence his music hasn't evolved at all. Some would disagree, but he's been stuck since 2008/2009.
These are our great artists.