There is a small class of mid- to late- 1960s movies--many of them offbeat as hell--that showcase Chicago and its architecture at a time when very few movies were made here. Among the best of the lot is Haskell Wexler's 1969's film Medium Cool, a caustic critique of the news media, politics and power.
Medium Cool is a landmark piece of filmmaking in which Wexler, a Chicago native, inserts his actors into the actual demonstrations and subsequent bedlam of the 1968 Chicago Democratic National Convention. Actress Verna Bloom rambling among the protestors in a bright yellow dress is unforgettable. My favorite part of the movie is the opening, seen in the clip above. Robert Forster and Peter Bonerz--who'd later find fame as dentist Jerry Robinson on TV's Bob Newhart Show--are television newsmen who callously cover a traffic accident on the still new-looking and desolate Eisenhower Expressway. But the cool part comes at 2:18 when they give their film to a motorcycle courier who speeds through the city to deliver the footage to the TV station.
With a foreboding, hypnotic score by Chicago-born bluesman Mike Bloomfield and Wexler's wide-angle camera seated behind the courier, we make a run down what looks to be the east-bound Ike to the Kennedy. I'm not sure where the jump-cut at 2:54 puts us; the modernist concrete building that appears on the right at 3:00 is a complete mystery to me. There a great shot of the courier crossing Michigan Avenue northbound with the Wrigley, Tribune Tower and Equitable Building rising to greet the camera much as it does today. The buildings stand out in relief then because there is almost nothing behind them--unlike today.
The movie holds a fair amount of goodies for Chicago architecture buffs. There's a great scene inside the geodesic dome-covered swimming pool of 400 E. Randolph, for instance. Wexler's brother, developer Jerrold Wexler, hadn't long completed the residential tower when the movie was filmed. The old Grant Park Bandshell just north of Roosevelt Road is seen at 1:29 in the clip below. It was demolished about a decade later.