This is kinda where I am with him. I've seen some good shit from him but regardless of politics the bro thing is annoying and gets old quick. The Pat Mcafee comp is pretty good, there are some clips out there from his show that are genuinely interesting, but I can't fathom watching him on a daily basis for hours on end. The clips of Gillis from his shows are better than his standup, more controlled delivery.
I saw clips of the trump-biden show that was pretty good and followed up by watching some Kill Tony and it was okay. I thought Kam Patterson was pretty funny, some of the others were too, but Kill Tony himself is painfully bro-y is just unfunny. To the extent there is some perception of Gillis as some maga idol it almost certainly comes from his close association with Rogan, Tony, and that crew (especially when Tony went full racist with a really stupid joke about Puerto Ricans). I've seen some clips where he sort of distances himself from that perception and I believe that he's far more normal than those shitstains. Either way, Derka's over the top love post is kinda creepy.