No matter how many times I see the names together, seeing Matthew Perry alongside Ron Perlman, Wayne Newton, William Sadler, and Kris Kristofferson still feels weird.
I suppose it's because Ron Perlman has always been the narrator, Wayne Newton is nearly synonymous with Vegas, and Kristofferson is the go-to-guy for grizzly older men. Matthew Perry is still Chandler in my eyes and ears, and Chandler wouldn't last five seconds in New Vegas, let alone become the leader of a gang.
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He might end up skinned and made into a jacket for the leader of a gang, but that's as close as he'd get.