Herbert

[Broccoli]

Thanks all.

M´Sharak said:
http://memory-alpha.org/en/wiki/Herbert_%28slang%29

I checked there first...it didn't help me on how they were making fun of someone by saying that.

 

[David cgc]

Alice: You look like a total Wally.
Wally: Excuse me?
Dilbert: We've started using your name as a pejorative.
Alice: Like "He's a total Wally," "I gotta take a Wally," that sort of thing.
Wally: It's catchy.

 

[M'Sharak]

Broccoli said:
Thanks all.

M´Sharak said:
http://memory-alpha.org/en/wiki/Herbert_%28slang%29

I checked there first...it didn't help me on how they were making fun of someone by saying that.

See also my post here for the part of the episode dialog which explains it. It isn't exactly making fun; it's the sort of thing you get when one small bureaucrat in a government office somewhere has the power to make absurdly unreasonable applications of the rules to the extent that his name becomes the label by which all similarly-inclined bureaucratic pissants are known. Your guess of "the man" in your original post was going in the right direction, but "Herbert" refers to a particularly "inflexible and officious nobody" subset of "the man" in the same way that "pigs" once referred to unfairly heavy-handed police officers. It's more derisive, critical and rebellious than merely poking fun.

 

[Plum]

^^^
Sounds about right!

 

[Mallory]

M´Sharak said:
It isn't exactly making fun; it's the sort of thing you get when one small bureaucrat in a government office somewhere has the power to make absurdly unreasonable applications of the rules to the extent that his name becomes the label by which all similarly-inclined bureaucratic pissants are known.

I'm guessing he worked for whatever passes for the Division of Motor Vehicles in that century. In which case he had centuries of behavior to fall back on.

 

[M'Sharak]

^ We reach!