Benicio smokes as nipples harden at the Che after party at 99 Sudbury

Benicio Del Toro held court in a corner of the 99 Sudbury (a.k.a. Greenhouse) patio last night, where he spent most of the evening with a giant cigar dangling from his mouth. The romantic Latin American music offered a nice change of pace that was well suited to TIFF hump day. Although Rachel McAdams and Matt Damon never made it to the red carpet, we did overhear a rather interesting exchange when actor Lou Diamond Phillips was asked what it was like to work with Benicio and Steven Soderbergh: “Eventually my anal sphincter loosened up.” Oh really? There are two very different assumptions we can pull from that statement; we’ll leave them both up to you, dear reader. Booze cans, Valentino, Evangeline Lilly and more from the Che party, after the jump.

It was only fitting that it was at a party in honour of Cuban revolutionary Che Guevara that we fell into conversation with some ex-hippies, who relayed stories of operating booze cans on Carlaw Avenue back in Toronto’s bad old days. While we were chatting with those gents, girls in extraordinarily short dresses hovered around giant Benicio. He may be somewhat leathered, but Del Toro has oozed sex appeal since his introduction to mass audiences in The Usual Suspects. The cigars, the girls, the hippies, the music—the only thing keeping us from mistaking the scene at 99 Sudbury for Che-era Bolivia was the weather. Teeth chattering and nipples erect, we all fussed with the heat lamps—much to the security guards’ chagrin. The whole party was a much-relished tranquil respite from the media circus over at the Windsor Arms. 99 was calm, democratic and peaceful.

Other celebrities who have whooped it up at the Mildred Pierce turned after-hours loft turned gym turned hot NYC Greenhouse space include Evangeline Lilly, Steven Soderbergh and Valentino. The venue has done a full 360 from its original roots. How appropriate that 360 Vodka was the presenting sponsor.—Jen McNeely