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Will & Grace · S04E14

Grace in the Hole

Still from Will & Grace S04E14

Summary

While visiting Karen's incarcerated husband, Grace re-discovers a handsome high school friend who's also doing time in prison, and despite Will's advice, she's soon dressing up and visiting the inmate while dreaming of a life together outside the Big House. Conversely, a sympathetic Rosario chides Karen for not standing by her man â€" and bets her boozy boss that she and pal Jack cannot stay penned-up together in the same room for three days without harming each other.

Guest stars

  • Brent Sexton as Prison Guard
  • Shelley Morrison as Rosario Salazar
  • Kirk Baltz as Glenn Gabriel
  • Cheryl Bricker as Sheila Slovinski
  • Steven Shaw as Judge