I've been listening to some old musicals lately, and one thing they've gotten me thinking about is the difficulty of writing a really laugh-out-loud funny comedy song. Of course most comedy songs are funnier in the theatre, with an audience, than they are on a record, so I'm not judging them fairly, but even in the theatre it's hard for a song to make me laugh as hard as funny dialogue or physical action -- there's just too much going on for a joke to "land" even in a first-rate song. "I Cain't Say No" is a funny lyric, but there are no spots for audience laughter, and the point is more to make us smile than laugh.
Also, while comedy songs are often loaded with rhymes and puns, those things don't always get laughs. If you look at the original cast performance of "Please Hello" from Pacific Overtures, in ten minutes of dazzling rhymes, there aren't many laughs from the audience except at the simplest jokes: the repeated "Don't touch the coat," and the first mention of "Detente" where the audience gets the topical joke. (Stephen Sondheim has also said that the song "Barcelona" gets its biggest laugh right at the beginning, with the simple exchange "Where you going?" "Barcelona.")
The songs that get the biggest laughs are, first of all, songs that have some built-in laugh pauses (either a literal pause or a repetition, like of the song's title, where we don't need to hear the lyrics). And they're often songs that don't have a lot of big jokes in them, but have some overriding comic idea. "Bewitched, Bothered and Bewildered" is, in my experience, a song that gets big laughs even on a record -- but only if it's sung by the kind of voice it was written for, a legit soprano voice. The gag is the contrast between the carnal sentiments of the lyrics and the sweetness of the melody and voice; when it's sung breathy and sexy, it is (again, in the performances I've heard) not a big laugh-getter.
And then there are some songs from unsuccessful shows that make me laugh harder than even comedy songs from some of the great shows. That's what got me thinking of this: I was listening to the cast album of the 1964 failure Bajour (about a band of Gypsies pulling an elaborate con on a naive anthropology student and her mother), and I was reminded that the song "Honest Man" always makes me laugh out loud.
It was added on the road as an eleven o'clock number for Herschel Bernardi (as the leader of the main Gypsy tribe) and Herb "Golden Girls" Edelman (as the leader of the Newark tribe). It's built around basically one joke, the "echo" joke where the characters repeat the last few words with a different meaning. But, because of the timing and the placement of the jokes, plus Bernardi and Edelman's delivery, I always, always laugh. And I bet I'd have laughed even harder with some of the visual business, like both actors taking off their hats as they sing "I swear by every hair on my head."
Are there any musical-theatre songs that always make you laugh?
Bajour is a pretty interesting show, though unrevivable since it's almost entirely built around negative ethnic stereotypes. It had great choreography by Peter Gennaro (who choreographed "America" and some of the other Sharks dances in West Side Story). The score, by a newcomer named Walter Marks, is quite good overall, entertaining even in the weaker songs, but Marks faded into almost complete obscurity after writing one other musical later in the decade (Golden Rainbow for Steve and Eydie, which produced Marks' only hit song, "I Gotta Be Me"). I think he wrote some material for Carol Burnett, and wrote the Merchant-Ivory flop movie The Wild Party. There were a lot of talented newcomers in the Broadway of the '60s who didn't quite make it, like Milt Schaefer (Drat! The Cat!), but Marks just sort of seemed to vanish, though I believe he's still alive.
The show was not an out-and-out flop, managing a run of about half a year. The problem with it, according to musical director Lehman Engel, was that it had two female stars, Chita Rivera (as a gypsy in charge of pulling the con) and Nancy Dussault (as the conn-ee). Rivera was better known, and you'd think that the "bad girl" would have the best material. But in fact, Dussault's material was generally better, and she was so good that she stole the show from Rivera. A lot of the tryout period was apparently spent trying to build up Rivera's part rather than fixing the fact that the male characters (except Bernardi) were weak.
Dussault and Bernardi proved they had the goods in another number that always makes me laugh, "Words, Words, Words," essentially a Vaudeville word-association sketch in musical form.
And, not comedy-related, but here's a sample of Gennaro's choreography, Chita Rivera dancing the title song. In this clip she sings it as well; Bernardi's character sings it on the cast album and in the script.