There's no doubt Drake has hit records. I think I told this story but I was in Toronto on tour the day after Back to Back dropped. A Philly dude in Toronto... It was tragic. After the show I went to this after party situation at this club. The DJ ran off about 20 Drake songs in a row. No other artist, just Drake. And the party stayed lit. I can never take that away from him. I'm not sure how many people have 20 straight jawns that can keep a party lit.
Now, how many of those will be timeless? How many will we be playing in ten years? Twenty? I don't know the answer. Does he have a Poison (BBD)? A Before I Let You Go? When I think of timeless songs, those are examples of songs where generations that come may not have been alive when the songs were created, but they play them at their functions and know all the lines nonetheless. Does Drake have those songs? Serious question. Not being shady at all. Rack City? Kiki? Hotline Bling?
Also, I still don't think he has a classic album. I see people say Take Care. I'd say Take Care is a classic Drake album but not a classic album on the level of Blueprint, Illmatic, Midnight Marauders, The Miseducation of Lauryn Hill, GRODT, GKMC, etc. Drake is amazing at creating dope ass singles but I don't think he puts together cohesive projects. I think he rides whatever wave is out (Little Brother, Wayne, Dram, Migos, Future) instead of being the wave and perhaps that's why it doesn't translate into complete projects.
What he does has made him rich and famous. So at the end of the day, none of what I think matters.