Putney Swope (Robert Downey, 1969) 
Putney Swope certainly hasn't aged that well and I'm never quite sure how effective a piece of satire it really was to begin with. There are moments in the film's take no prisoners approach that work successfully, most notably the advertising sequences, but the larger issue of race and late 60s radicalism don't feel that fleshed out and are there to be taken advantage because they can. Downey may get some credit for addressing the issue at the time but his execution, while barbed, comes off as too superficial and amateurish to be called great satire. Some of this can't be faulted too much because the film is a low budget indie but the execution leaves something to be desired. The story centers on the title character, the token black man at an advertising agency. When the president of the agency dies, and with the other board members unable to vote for themselves, Swope accidentally gets voted in because the others think that no one else will vote him in. Swope proceeds to fire everyone except one token white and replace the board with black radicals. Swope vows a new form of advertising, to get truth and soul out. This is where we get the commercials featuring an orgy used to sell airlines and a limbless man praising an insurance company. The faux ads are by far the cleverest satire in the film, as the stiff and unoriginal portrayal of Swope and his radical counterparts falls flat. Swope eventually becomes no better than the men he replaced, being consumed with the greed and hubris that come with his "remarkable" ideas. That Swope's comeuppance is never really earned fuels the uneven nature of the film.