Every single time .
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Michael Ian Black is the kind of guy to tell you he is famous and that's why you must know who he is. He openly said he does that to people in airports.
That should tell you everything about how pathetic his existence has been and why he hates others.
tfw your Filmography zenith is your credited role in Wet Hot American Summer.
Hey now, he managed to get 7 whole episdes of his show on Comedy Central before it got cancelled for being unwatchably bad and unfunny.
This being the network that gave Amy Schumer's show 5 seasons and Sarah Silverman's 3 seasons, that's a super high bar!