Michael Ian Black and Josh Malina’s Sad, Sad Conversation

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“It is sad to be old and still be in show business. This business we call show,” muses The Go-Go’s Jane Wiedlin on Michael Ian Black’s sadsadconversation YouTube channel. Created with Josh Malina back in April, Black’s truly depressing video conversations on aging and creativity have since expanded to include topics like Rob Delaney’s stress-induced alopecia, Sarah Thyre’s hoarding neighbor, and Martha Plimpton’s anxiety about being known in the comedy community enough to even participate. Watching a wild-eyed Steven Weber find a spider in his hotel room and launch into a conversation about Brando is almost too real, though not as unsettling as watching Steve Agee hold a fake gun to his head. “That tiny crystalline moment solidified for me the career choices I would be making from that point forward,” Black recalls about his decision to go into acting based on his experience in a childhood play. “Important, adult decisions were made that summer by a boy that had not yet fully mastered the art of tying his shoes…today I say to that child, maybe finance would have been a better decision.”