Watch Winona Ryder, Chevy Chase and the Most Random Cast of 2011 in This Stay Cool Trailer

Here at Movieline, we've seen some pretty random casts take the screen. Take for instance, the WTF-ery of The Big Bang (James Van Der Beek, Antonio Banderas and Snoop Dogg) or the brain teaser talent pool on Dorothy of Oz (Lea Michele, Kelsey Grammer and Patrick Stewart). But what can possibly be said about a trailer featuring Winona Ryder, Hilary Duff, Chevy Chase, Jon Cryer, Josh Holloway and Sean Astin acting out a second-rate Grosse Point Blank plot? Take a look at the trailer for Stay Cool and then we'll try to articulate our thoughts.

First, I bet you didn't see Sean Astin's over-the-top portrayal of a wrist-wagging, pink helmet-wearing best friend coming. Second, this movie! Written by Mark and Michael Polish, Stay Cool centers on a 30-something author who returns to his home town to deliver the commencement speech at his former high school. There, Henry (Mark Polish) finds himself tangled in a mess of nostalgia, potential flames (Winona Ryder as his high school crush-turned-local pharmacist and Hilary Duff as a "sexy" high school senior) and coming-of-age confusion, none of which are helped by his friends Big Girl (that is seriously the character name given to Sean Astin) and Wino (Josh Holloway).

Two years after Stay Cool's 2009 Tribeca Film Festival premiere, the Ted Smith-directed comedy finally graduates to theaters September 16.

VERDICT: Another high school reunion for which I will RSVP "No thanks."

[via MovieWeb]