Molly discovers that her husband is cheating on her, tipping her over the edge and sending her to her building's roof to drink beer. In this state she encounters a homeless man who distracts her from her current malaise, and perhaps has something to teach her too.
The plot summary on the IMDb page includes the word "whimsical", and it is a word that probably appeared all over the script as stage- direction notes – "more whimsy", or "distant look & half-smile"; this is a film that really is not short of it. Watching as many shorts as I do, there are those gently quirky ones that do manage to pull off the mix of quirky, semi-comedic oddity and pull the heartstrings at the same time; when it works, it looks pretty easy and natural – because this is the tone of the short, however it is not an easy balancing act, and unfortunately Lady and the Bum shows this.
The film gives us two damaged characters (one still raw from the pain) and with no other connection between the two people, and the one recently pained learns a lesson of sorts from the odd homeless guy that she wouldn't have otherwise talked to. As a narrative it needed a lot to make it work, and instead it plays too much to the whimsy and oddity of it all, hoping that this will carry it, rather than building a strong base and bringing the viewer into the inside of it. As a result it feels like it is pushing quirky and whimsy but without any reason for us to be emotionally affected by it – and indeed I was not. There does appear to be a good heart behind it, but just not one that is tangibly within the content of the film, and it does rather come across like it knows what it wants to be – but doesn't really know how to make it happen.