There’s a problem with comedy songs that they outstay their welcome almost impossibly early, sometimes before the end of the first listen. The problem, really, is that all too many comedy songs forget to be songs, and instead focus on the comedy, and it’s only the truly great jokes that manage to stand up to repeated revisits in the same way that we tend to want to revisit songs over and over again. All the more credit, then, to Blossom Dearie’s “I’m Hip,” which is undoubtedly a comedy song, but one that’s entirely enjoyable as a song even if you don’t get the joke.
A lot of that is down to Dearie’s vocals, which are as light as ever; she always had a tendency to sound a little like a comedy character at the best of times with her very particular voice, but with a song like this one, that feels even more the case (Lines like “Like you notice I don’t wear a beard” gain a second meaning with her girly vocal). Here, she helps the joke go down with the fact that she sounds like she’s blissfully happy, in on the joke but with no malice behind it, which feels important for reasons I can’t quite put my finger on; maybe a more restrained, hipster detachment would be funnier on first listen, but would over-egg the comedy pudding…? Nevertheless, Dearie manages to somehow defuse whatever meanness may be inherent in the song, which goes a long way towards giving the song/joke a longer life, as well as just making it a joy to listen to; her sing-song take would be fun even if you couldn’t understand what she was actually saying.
(It also helps, I suspect, that (a) the jokes are funny, and (b) the jokes are also pretty silly; “Bobby Darin knows my friend” as a boast? One of the writers on this song was Bob Dorough, who wrote all the songs for Schoolhouse Rock, and there’s a shared goodwill between those songs and this one, a lack of teeth or desire to cause genuine upset.)
Also light, and subtly helpful in making this a repeatable pleasure; the musicians in the background, with Dearie on piano (so light, playing it as punctuation almost, letting her voice carry the majority of the melody when she’s singing) and some lovely brushwork on the drums keeping time and offering a backbone of style but, thankfully, little else right up until the big cymbal finale. In many ways, this is popcorn music, fluffy and pleasant and entirely throwaway, but done with such style that it ended up sticking around after all.