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Stay Cool

4.820111h 34mPG-13MovieComedyRomance

A successful author is forced to confront an unrequited high school crush when he returns home to deliver a commencement address to graduating seniors. Shasta O'Neil, a sexy high school senior flirts with the visiting author and invites him to the prom.

DirectorMichael Polish
WriterMark Polish

Where to watch

Amazon Prime VideoAmazon Prime VideoCraveCraveAmazon Prime Video with AdsAmazon Prime Video with AdsHooplaHooplaTubi TVTubi TVPlexPlex
Availability shown for Canada · rights vary by country

Cast · Directed by Michael Polish

WRWinona Ryder
Winona Ryder
Scarlet Smith
MPMark Polish
Mark Polish
Henry McCarthy
SASean Astin
Sean Astin
Big Girl
HDHilary Duff
Hilary Duff
Shasta O'Neil
JHJosh Holloway
Josh Holloway
Wino
JCJon Cryer
Jon Cryer
Javier
CCChevy Chase
Chevy Chase
Principal Marshall
JCJessica St. Clair
Jessica St. Clair
Darcy Portola
FCFrances Conroy
Frances Conroy
Mrs. Leuchtenberger
MBMarc Blucas
Marc Blucas
Brad Nelson
JCJoanna Cassidy
Joanna Cassidy
Mrs. Smith
DWDee Wallace
Dee Wallace
Mrs. McCarthy

More from Winona Ryder · Lead actress

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Beetlejuice Beetlejuice
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Bram Stoker's Dracula
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More from Mark Polish · Co-star actor

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More from Michael Polish · Director

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Stay Cool — streaming FAQ

Which OTT platform streams Stay Cool?

Stay Cool is streaming on Amazon Prime Video, Crave and Hoopla in Canada, and available to rent or buy on YouTube. It's not currently on Netflix.

Is Stay Cool on Netflix?

No, Stay Cool is not on Netflix in Canada as of November 2026. It's currently on Amazon Prime Video and Crave.

Is Stay Cool on Amazon Prime Video?

Yes — Stay Cool is included with an Amazon Prime Video subscription in Canada as of November 2026.

Where can I watch Stay Cool for free?

Stay Cool is available to stream free (with ads) on Hoopla and Tubi TV in Canada.