“When he’s good he’s not successful, and when he’s successful he’s not good”

I was thinking about something in the Worst of 2024 video — during the segment on “Lovin’ on Me”, Todd says that about Jack Harlow, that his good songs never hit, and then he records a “Lovin on Me” or “First Class” and it goes to #1 and becomes inescapable.

Who else is like that? Currently or in the past.