Sydney Pollack's Tootsie (1982) at Butler Field in Chicago's Grant Park. It was the final film in this summer's Chicago Outdoor Film Festival—in July I saw Billy Wilder's Sunset Boulevard—and the first time I'd seen my favorite of Pollack's movies on a big screen. The appreciative audience surrounding me didn't hurt.
Yesterday* I discovered the following Late Show With David Letterman clip, from December 22 of last year, on YouTube:
* Almost 14 years later I discovered that the original clip had been pulled from YouTube. The link above, which I can't embed on Blogger the normal way, will have to do.