MUSIC I Sasha Grey DJ Set at the Drake
The Drake continues to make good use of their extended last call license with a performer -- isn't that just the perfect word? -- who's become quite popular of late. Sure, Sasha Grey may be known for her work on screen -- both pornographic and otherwise -- but who knows? -- If she was able to transition from the adult scene to mainstream movies and television, perhaps she can DJ too.
The Drake Hotel, 1150 Queen St. W, $5 ($10 after midnight), Doors at 10pm

DEBATE I Mayoral Debate at Innis College, U of T
If you're not into late night drinking with porno-starring DJs, then a mayoral debate just might be your thing. As the election date creeps closer, these debates are going to start to matter just a little more. Plus, you'll get to see Rocco Rossi squirm as he tries to explain where the money's going to come from to build his "Toronto Tunnel." Oh, and its moderated by John Tory, the guy that would have won had he entered the race.
Innis Town Hall, 22 Sussex Avenue, Free, 7-9pm

FILM I STIFF: A Celebration of Queer + Sex Positive Films + Filmmakers @ TIFF
Sometimes the event write-ups do the work for you. Case in point: "From the people who brought you Hot Cocks at Hot Docs comes STIFF, a celebration of queer + sex positive films + filmmakers at the Toronto International Film Festival. From Bruce La Bruce, John Cameron Mitchell, Gregg Araki, Apichatpong Weerasethakul, Francois Ozon, Xavier Dolan, and Dustin Lance Black to the bisexual bounty that is "Black Swan" to a documentary on Yves Saint Laurent...this TIFF is very queer indeed." Event moved from the Beaver to Wrongbar.
Wrongbar, 1279 Queen St. W, Free, 10pm-4am

TRIVIA I Woo Hoo! Classic Simpsons Trivia
I could hardly believe it when I found out yesterday that the Simpsons has been on for over 20 years. If you were a fan during the first half of this run, tonight's trivia challenge may be right up your alley. "Woo Hoo! is three cromulent rounds of 20 questions about Simpsons seasons 1-11 (ending with 'Behind The Laughter'), plus three classic episodes on the big screen. Team up with up to six friends for maximum fun, and you could win delicious prizes." There's also cheap beer and no cover. So, yes, woo hoo!
The Ossington, 61 Ossington Ave., Free, 8-11:30pm

SEWING I Sewing 101
The inclusion of this event isn't some bit of hipster irony. The reality is that learning to sew is very useful in general, but if you're interested in fashion, it's an absolute prerequisite for any serious foray into the field. And though it's $200, that's for a total of six classes. Runs on Tuesdays, Sept 14 - Oct 19.
Harbourfront Centre, 6:30pm - 8:30pm

Photo by David G. Tran of the blogTO Flickr pool.