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Macho Caballero

Derek Sheen

Stand Up! Records · 2020

A miserable, highly specific comedy special about turning fifty.

Watch on Stand Up! Records(opens in a new tab)

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.

The set list

5 bits

  1. Turning 50 and joining a gym

    Compares joining a gym at 50 to choosing to die dragged by a low-speed treadmill, framing the milestone as going through a confusing second puberty marked by existential dread and night terrors

  2. Toilet injury

    Recounts slipping and falling off a hotel bathroom toilet like a Looney Tunes cartoon, hobbling himself and forcing the cancellation of an important show

  3. Magic Bullet

    Draws an elegant comedic parallel between the kitchen blender and the JFK coup

  4. Seattle bar blackout

    Tackles addiction by detailing a night out in a Seattle bar that spiraled into a six-day blackout

  5. The shooting death of a clown

    Finds inherent dark humor in the demise of a clown

How it plays

Tone
Acerbic, cynical, dark, vulnerable, and self-deprecating
On stage
Acerbic, self-deprecating, and observational comic blending cynical wit with earnest vulnerability and manic storytelling
Pace
Signature high-energy delivery with brisk pacing
About
aging and turning 50, physical decay and bodily changes, alcoholism and substance use, masculinity in a modern cultural landscape, generational dynamics between Gen X, Millennials, and older generations

What the critics said

Richard Lanoie of The Serious Comedy Site praised it as superb, consistently interesting, and funny, remarking that its craftsmanship was elegant enough to make other comics jealous with virtually no weak moments

In the room: Focused atmosphere emphasizing Sheen's engagement and rapport with the crowd

Summed up from reviews, articles and listings. Sources: allmovie.com, watchwhatwhere.com, en.wikipedia.org, theseriouscomedysite.com, allmusic.com, thestranger.com.

Backstory

Turning 50, navigating physical aging and body changes, sobriety after alcoholism, and managing depression with medication

Details

Released
Taped
2019, Clock-Out Lounge, Seattle
Where
Stand Up! Records
Director
Alek Roslik
Honors
Peaked at No. 6 on the iTunes comedy chartPeaked at No. 7 on the Amazon comedy chart
Topics
Before
Disasterbation (2017)
After
Unrelatable (2026)

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