As Joe Rogan mentions (in the clip below) the joke works because many people have thought about it at some stage or another 
As if by clockwork, the media Woody says is bought launches a tirade against him. You couldn’t make it up 
So, he wasn’t actually acting in Cheers.
Humour is subjective. I never found any in that clip.
I didn’t find any of that 6 minute clip remotely funny, not even mildly amusing - it was cringe-worthy. I was wanting to switch off from about 2 or 3 minutes in, but I stuck with it to find out where the joke came in - it never came!
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Some of them really should just keep their mouths shut, shouldn’t they?
I really liked him in True Detective but what a self-indulgent, boring crock of poop that was…. 
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