I remember when Vice was interesting and actually politically incorrect, in 2007 they had an article about how to score with a "tranny" at a party, which was presented as a lark worth having, but still done in a gross out fashion like "isn't this totally outrageous!?"
And in their articles where they would rate people's fashion they dissed a black guy's dreads as "Snoopy Ears" once.
I first noticed a tonal shift though in 2013, when they had an article about a guy attending a screening for critics of the Jason Statham movie The Mechanic at the Playboy mansion, the author of the article made it clear that he could not have cared less about the movie he was being paid to watch and ditched it so he could learn what it was like to "take a crap" at the Playboy mansion and he dissed the whole mansion as rundown and shitty, the whole thing felt very obnoxiously smug in that hipster way.
That same year they also complained about the Universal Studios Halloween Bill and Ted stage show as being homophobic and in response Universal canceled the long running show, so from joking about trannies to being such a whiny tit they caused the canceling of a long running and well loved stage show, costing people jobs.
So the stage was set for in 2014 when Gamergate happened and every website went into full "shut it DOWN!" mode including Vice.