The new spot, created by the pro-Hillary Clinton Super Pac Patriotic Artists and Creatives, is an unabashed, almost joyous attack on the Republican candidate. It opens with a mosaic of TV screens featuring soundbites of various talking heads, including prominent members of the Republican party, calling Mr. Trump a narcissist.
Ms. Simon's song then kicks in and the ad goes on to employ a now familiar anti-Trump advertising device: turning the candidate's own words against himself by recycling moments such as when he mocked a disabled New York Times reporter or an E! interview in which he admitted he couldn't say that he treated women with respect. It also piles on image after image of Trump-branded products, from steaks to casinos to buildings and water bottles.
According to the ad's YouTube post, this is the first time that Ms. Simon has agreed to use her song in a political ad. (It appeared in advertising at least once before in a U.K. ad for Dunlop tires.) But as revealed in a Forbes piece by Melinda Newman, there's a notable bit of new material: a freshly recorded line from Ms. Simon herself, in which she replaces the lyric "your scarf, it was apricot" to "your face, it was apricot" just as the spot projects a close-up shot of Mr. Trump's neon orange puckering mug.
In fact, the ad seems to have a ball tossing in unflattering, embarrassing images of the billionaire. Starting at 1:24, for example, it cuts together a voiceover of Trump calling himself "handsome" with side-by-side images of his wispy hair flying about his head like Marilyn Monroe's skirt in "The Seven Year Itch." When Ms. Simon sings the line "and all the girls dreamed that they'd be your partner," the ad unveils a triptych of wedding photos of Trump and his three wives, followed by a meme-ish image of him riding horseback with a shirtless Vladimir Putin.
It's not all about his looks, though. The ad mixes in several moments that question Trump's leadership abilities -- and humanity. One scene finds him at a rally, pointing at an audience member and saying "Look at my African-American over here." Another in which he calls himself "the greatest jobs president" is followed by a David Letterman segment during which the host points out that Trump ties are made in China.
It all closes on an image of Trump, arm raised in a "Heil Hitler"-style pose, before revealing the title card: "Donald Trump. Dangerously Vain."