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Derrick Stroup: A Joke About The Midwest

May 12, 2026
Derrick Stroup, a stand-up comedian and writer known for sharp observational takes on American and regional life. He riffs on small-town charm, a Kansas partner who’s easily impressed, and playful regional rivalries. He also jokes about Midwest remoteness, scarce medical care, and Kansas’s extreme flatness and prison gag.
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ANECDOTE

Partner From A Town Of 89 People

  • Derrick Stroup describes his partner from Kansas as easy to impress and from a town of 89 people.
  • He contrasts his Alabama background with Kansas, showing cultural difference through the elevator reaction and jokes about small-town life.
INSIGHT

Midwest Feels More Remote Than The South

  • Growing up in the South taught Stroup he lived 'in the middle of nowhere' until visiting the Midwest revealed even more remote places.
  • He riffs that Midwest towns lack medical care and feel like the Oregon Trail, highlighting surprising rural extremes.
ANECDOTE

Imagining Kansas Prisons With Nowhere To Hide

  • Stroup jokes Kansas is the flattest place he's seen and imagines prisons there where escapees are visible all weekend.
  • He sketches guard tower banter watching an inmate give up and reading the address after running three days.
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