"Bob? Ain't that a bitch!" - Prince
Tim Robbins was condemning the Vast Right Wing Conspiracy before Hillary made it cool. He wrote, directed and starred as the titular Bob Roberts in 1992. Bob Roberts was a smiling, good looking and charismatic fount of pure, twisted hilarious conservative Republican evil.
Politics aside, Robbins made a really outstanding and clever movie with a strong vision, and no small number of laughs. He took every bad or bad sounding thing from the original Reagan-Bush years, and rolled it into one almost believable conspiracy arch. You see, the damned conservatives were looting S&Ls to invest in drug running from Central America to raise money to support the Contras- and enrich themselves, naturally. These couple of sentences may not sound that promising for a movie comedy, but the skill of the writing puts it all across.
Particularly, he created an exceptionally clever and comedy worthy frame for the whole thing. Bob Roberts is a pop star, writing folk style songs to express his fanatical and callous right wing views- which form the basis for a candidacy for the US Senate. This gives him endless opportunities to invert Dylan, the classic model for this stuff, for example his album "The Times Are Changin' Back." He also has a video parodying the famous cards-in-the-alley video, in which Bob Roberts now advocates making millions "by any means necessary."
One big aspect that makes the whole thing work is the quality of the songs that Tim and his brother David Robbins wrote. Just as songs, they are more interesting than anything Dylan himself has done in 20 years. They're pretty catchy, have fairly simple but effective and wide ranging arrangements, and the stench of sulfur from hell emanating from every single one. For example, he really embodies the war on drugs in "Drugs Stink" in which he encourages the literal lynching of drugs users and sellers. "Be a clean living man with a rope in your hand." Not only that, it's a catchy little tune.
Putting it in another context, I'd rate the songs from Bob Roberts notably superior to the actually good songs from the classic Spinal Tap. Both movies feature songs specially written as parodic content in character. Tap had some grooves, but the brothers Robbins wrote much more intricately clever songs. This not surprising in that Tap songs were Zen songs written in the voices of stupid people. Roberts is a wicked smart dude, much more interesting. The tunes are more developed, the arrangements not purposely cheesy. The words of "Complain" are more sophisticated than those of, say, "Sex Farm". Not only are all the songs strong, but individually distinctive. Each one is a unique stylistic creation, not quite like any other.