that's only because he still has weird remnants of fat/loose skin around his face. once he loses the turkey wattle hanging from his chin he should look much better.
Fat doesn't hide the wrinkles, it stretches your skin out. When people lose significant weight they look like 2 lbs of shit in a 50 lb bag and it looks odd. It looks odd until they get things like face lifts and tummy tucks, that is why the procedures exist.
I think Al Roker looks better skinnier though. That Drew Carey pic looks especially bad, almost like his suit doesn't even fit him.
I think he would look a lot better if he got a suit that fits him. Pants way too big and way too long. Jacket at the least needs to be tapered. Those peak(?) lapels look a little big. In the first pic he's under studio lighting so he has a slightly orange glow. Might be a little blue/orange thing going on with that white stripe in the middle. In the second pic he just looks too pale.
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