The premise didn't sound very original at all, then again that is something that one comes to expect from the Screen Songs cartoons the more that is seen of them. It also sounded like there was a danger of 'Win, Place and Showboat' feeling like it was produced ten plus years too late. Having said, the showboat setting did have potential and it is not hard to see why vaudeville was such popular entertainment for a while and why it is historically significant.
'Win, Place and Showboat' was another cartoon from the Screen Songs series that was a bit of a mixed bag in execution. It is a long way from a great cartoon, with some of the inevitable traps being fallen into, or one of the series' best. Too standard, safe and old-fashioned for my liking generally. 'Win, Place and Showboat' is also a long way from awful, with a fair share of good things and it was more tasteful than feared, and is not one of the series' worst. Others did worse at being too cute, being humourless, dull and being distasteful.
Am going to talk about the good things first. The animation here is good on the most part. Especially the vibrant colours and equally loved the background detail where a lot of care went into it, the setting looks handsome yet has grit too. The incidental music is even better, very lushly orchestrated and full of character rhythmically. The song is pleasant and catchy enough, if not one of the series' most memorable.
Did think that a nice job was done with a few of the vaudeville acts, which the cartoons does well in capturing the essence of, though they are typical. The frog quartet was especially enjoyable as was the climax, one of the few in the series to have a sense of jeopardy. Some of the sight gags do amuse and that 'Win, Place and Showboat' made an effort to be careful to not cause offense by having colourful animal characters instead of racial stereotypes, or any kind of stereotypical, for the acts.
On the other hand, the story is very thin and formulaic, with inconsistent pacing. Lively in the first two thirds, and the climax is fun, but generally the singalong is on the corny and old-fashioned side (though it is not one of the singalongs that doesn't gel with the rest of the cartoon).
The gags have amusing moments, but are pretty standard, there could have been more and some groans are induced. There are better gags involving chickens in the series. The elephant running joke gets repetitive, so one doesn't blame the audience reaction at the end. While most of the animation is good, it is quite rudimentary and lacks refinement in the singalong portion.
Concluding, watchable but again mixed feelings. 5/10.