13. Fiona Apple
Fiona Apple is another name that will not be familiar to readers under 20, but trust us; Fiona was quite huge back in the mid-1990s. Her first album was a ginormous hit back in 1996, called Tidal and packed with a bunch of hits, the biggest of which was definitely Criminal, vide for which caused quite a ruckus back then.
With Fiona, it is quite easy to put the finger on the moment when things started going downhill. It was the infamous on-stage meltdown in 2000s, when she ended up crying on stage and apologizing to the fans. She took a break from it all after that and only in the last few years has she been trying to mount a comeback.
And we have to say that it’s not going too great. Perhaps it has something to do with the fact that she keeps getting arrested for possession of pot and hash or with the fact that she canceled an entire tour because her dog was ill.