As far as modern history goes, Booker T and Corey Graves lead the pack for me. For very different reasons as well.
Book takes the cake for rambling and saying off the wall dumb shit, in addition to his voice itself being pretty grating. Corey on the other hand tries too hard to be the smartest guy at the table and put himself over at the expense of his partners. He forces contrarian takes, which is pretty well established trope for heel commentators, but he doesn't have the same penchant for self-deprication and parody that former greats like Bobby Heenan and Jerry Lawler had. He's really just distracting and adds very little value as a commentator to me.
JR definitely also deserves a mention. He's obviously way out of touch and oftentimes can't help from burying the product. That is when he's managing to focus on the action and not trailing off on his own side tangents. He's nowhere near the commentator he was in the 90s and 2000s, and thankfully he's not as much of the product these days.
Book takes the cake for rambling and saying off the wall dumb shit, in addition to his voice itself being pretty grating. Corey on the other hand tries too hard to be the smartest guy at the table and put himself over at the expense of his partners. He forces contrarian takes, which is pretty well established trope for heel commentators, but he doesn't have the same penchant for self-deprication and parody that former greats like Bobby Heenan and Jerry Lawler had. He's really just distracting and adds very little value as a commentator to me.
JR definitely also deserves a mention. He's obviously way out of touch and oftentimes can't help from burying the product. That is when he's managing to focus on the action and not trailing off on his own side tangents. He's nowhere near the commentator he was in the 90s and 2000s, and thankfully he's not as much of the product these days.