Shooting later this month in Santa Clarita, California, "Stay Cool" is written by Mark Polish and Michael Polish.
The comedy focuses on a successful author (Mark Polish) who returns to his hometown to deliver a graduation address at his high school and has to confront his high school crush ( Winona Ryder).
According to The Hollywood Reporter, Holloway will play another of the author's high school classmates, a former jock and the crush's ex-boyfriend.
Also on board for the comedy, set to be directed by Michael Polish, are Sean Astin, Chevy Chase, Jon Cryer and Hilary Duff.
Best known as Sawyer on "Lost," Holloway co-starred in the thriller "Whisper."
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