Macho Caballero

Derek Sheen · 2020 · Stand Up! Records

Macho Caballero

A miserable, highly specific comedy special about turning fifty.

April 23, 2020 TV Special

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Derek Sheen turned 50, and his body immediately started giving out in ways that defy medical logic. His fourth full-length release with Stand Up! Records captures a Seattle stand-up who is deeply annoyed by the aging process. Rather than easing into middle age with dignity, Sheen is left trying to figure out why his body is suddenly growing its own set of breasts, why he’s waking up from spider nightmares with soggy sheets, and how he managed to injure himself so severely falling off a toilet that he had to cancel a gig.\n\nIt is a specific, self-deprecating hour of physical decline and petty grievances. Recorded by Alek Roslik and released in the spring of 2020, the special features Sheen positioning himself as a stranded Gen-Xer trapped between the pleated-khaki older generation and the hyper-earnest Millennials he both defends and mocks. He takes aim at his own late-onset marijuana use, the slow death of joining a gym at 50 (which he describes as merely choosing to be dragged to death by a low-speed treadmill), and the absurdity of his generation giving Whitesnake a Grammy. The performance is heavy on bleak, highly visual storytelling, showcasing a veteran road comic who has spent years touring with Patton Oswalt and Brian Posehn, refining a style that treats personal misery as an inevitable punchline.