This song has gotten made fun of endlessly for a reason: the story it tries to tell is patently ridiculous on its face and has about a dozen holes in its plot that only occur to you after you think about it for a while. It also makes both characters sound like shallow, self-involved assholes, which kind of works against its attempts to be romantic, and the superficial ‘interests’ listed on the chorus don’t help that impression. There’s also the bizarre phenomenon that many people think this is a Jimmy Buffett song, which I can only attribute to the fact that his biggest hit also referenced a mixed drink in its title. I mean, seriously, they aren’t even in the same genre—Buffett is early Pop-Country, whereas Rupert Holmes is an Easy Listening/Soft Rock songwriter in the Barry Manilow vein. And frankly, Buffett generally wrote better tunes than this thin, tinny glorified jingle…seriously, Manilow got a lot of crap for having started out writing commercial jingles, but at least his pop songs couldn’t be mistaken for one. Holmes actually had talent…he would later write the book and score for one of the most innovative and interesting Broadway musicals of the Eighties, The Mystery of Edwin Drood…but for some reason his career as a Soft Rocker was consistently terrible. It’s really a shame that this song (and, to a lesser extent, “Timothy”) became his most enduring public legacy instead of his far superior Broadway work. As for this song, it has provided multiple generations of comedians with an extremely rich target for ridicule, but as far as I can tell, that’s pretty much its only value.
Verdict: Bad (what a surprise).