Special Presentation: The Reach, 3 p.m., Ryerson Theatre
A corporate shark played by Michael Douglas shoots and kills someone in the Mojave desert, and his young guide (played by Jeremy Irvine) is there to witness it. The problem? Jeremy isn’t willing to cover it up, leading to a dangerous game of cat and mouse.
Gala Presentation: Pawn Sacrifice, 6:30 p.m., Roy Thomson Hall
In one of chess's most iconic moments, Bobby Fischer takes on Russian Boris Spassky in 1972 for what was billed as “The Match of the Century” in Reykjavik. Tobey Maguire and Liev Schreiber star as the champion chess players.
Special Presentation: American Heist, 7 p.m., Princess of Wales Theatre
Special Presentation: October Gale, 8 p.m., Visa Screening Room
Patricia Clarkson's lonely character finds a young man (Scott Speedman) washed ashore and takes him to her remote cottage to nurse him back to health. Unfortunately, unbeknownst to her, the man who attempted to kill Scott (Tim Roth) is on his way to seal the deal.
Special Presentation: The Voices, 9 p.m., Ryerson Theatre
Canadian star Ryan Reynolds plays a young shipping clerk who goes off his prescribed antipsychotics in this horror-comedy from graphic novelist Marjane Satrapi (Persepolis).
Gala Presentation: Escobar: Paradise Lost, 9:30 p.m., Roy Thomson Hall
Drug cartels have long been an intriguing subject, and TIFF's got an addition for the bank of non-stop thrill rides. Josh Hutcherson plays an American surfer who serendipitously finds the girl he’s been dreaming of. The twist? Her uncle is Columbian drug kingpin Pablo Escobar (played by Benicio del Toro).
TIFF at Night:Star-studded soirées, open late, Storys, America, Soho House Toronto
The best way to catch a glimpse of an A-list star after a splashy premiere is to steal a peek at stardom at some of the hottest festival haunts. Storys, Trump Hotel’s newly-minted America and Soho House are all slated to have an ongoing swell of parties with some of Hollywood’s biggest stars, so they’re among the hottest spots to do some of the fest’s best people watching. For more hotspots to see, check out our three-part video guide!