Tyga
Tyga had a hit song or two in the rap world, but he really peaked when he started dating Kylie Jenner. The controversy around the couple was juicy enough to keep his music career alive. Think about it... when was the last time you heard about him? Their breakup?
Post-Kylie
Let's be real: he's released music but hasn't gotten any cred since his break-up with the young billionaire. Jenner has since moved on and had a baby with fellow rapper Travis Scott, who already had a decent enough career. Tyga probably won't stop rapping, no matter how unpopular he gets.