10 Musicians Whose Careers Were Destroyed By Just One Song

The writing was really on the wall for this one the moment that Macklemore beat Kendrick Lamar for Best Hip Hop Album at the Grammys, then proceeded to text him and apologise for the travesty.

Beloved by indie hip hop fans for much of the noughties, Macklemore was a hard-to-categorise rapper best described as the human embodiment of Internet culture from 2010-2013.

Sincere and well-meaning, childish in his humour but often surprisingly thoughtful if ham-fisted in his lyrics, the technically superb rapper had a string of wildly different cult hits from 2011-2014. Thrift Shop was a goofy self-parody slice of pop rap, Can’t Hols Us was an anthemic club banger, and Same Love was a corny but good-meaning attempt at LGBTQ+ ally-ship.

But it had to end eventually.

The too-sincere rapper released White Privilege II in 2016, and the well-meaning but tragically overlong and cringeworthy track it spelled the end of his brief tenure as a massive mainstream rapper. Needlessly lengthy and overstuffed, the song attempted to be a hard-hitting critique but ended up a limp softball, and the hip hop community’s derisive reaction landed the rapper an impossible-to-shift reputation as a cornball.