How the f*** did I forget Slick Rick
smooth delivery was definitely his best strength, he rode every verse like a wave
Not to mention he was Snoop's OG, like he covered La Di Da Di on Doggystyle, which never happens in Hip-Hop, smoothness leads to smoothness
Literally Q-Tip
Smiley
He said smoothest not gayest
used to be kanye west. never heard anyone rap into the HOOK from the verse so effortlessly. now a days i would say the wale. mac miller , currency comes to mind

Anybody from this classic. But I'd go with CL Smooth.
Sauce Money is up there too. And Evidence too but from Cats & Dogs onward.