The guy is all sorts of recognizable due to his time as James 'Sawyer' Ford on Lost, but do you know that Josh Holloway is also the dude who got his start in Cryin'? Yes, he played the jerky guy who smiled and then stole Alicia Silverstone's bag, and she had to chase him down and give him a good kick. (Watch it above.) He's come a long way since purse stealing! Now The Hollywood Reporter posts that he's joined the cast of Stay Cool.
This is the Polish brothers feature that Hilary Duff joined recently -- where a successful author (Mark Polish) goes home to give a high school commencement address, gets hit on by a high school girl (Duff), and has to face his unrequited teen crush (Winona Ryder). But now Holloway has been added to the mix as a former jock who used to date Ryder's Scarlet Smith. Production should begin soon in California.