In the 1930s-50s, Marie Wilson essentially played the same character again and again...a ditzy blonde who made Gracie Allen seem like a Nobel Prize winner! Occasionally, this sort of thing can work but often she just comes off as annoying when you see her films today....and she's incredibly annoying in "Sweepstakes Winner".
The story begins with Jennie arriving in the big city and she's looking for Jinx and Tip (Charley Foy and Allen Jenkins). They think she's with the law...but someone ill-advisedly suggested to her that she find the two gamblers so they can help her locate and buy a specific horse, Firefly. Unfortunately, the pair are not only hapless gamblers but really unsavory jerks who repeatedly do things which could get them sent to prison. But Jennie is so brainless that she never notices as they rob her again and again and again.
In addition to Wilson being tiresome, the film also has a major problem when it comes to Jinx and Tip. At times, they seemed to be comic relief...there for fun and silliness. But other times the pair are downright evil....to the point where you cannot like them and you only want to see them in prison. The characters clearly were poorly written and should have just been comic relief...but they wanted them to be silly AND sympathetic AND evil...a combination that just didn't work.
Overall, a very difficult film to watch, as it just is hard to keep watching. My wife kept hoping I'd give up...but I apparently like pain and kept watching up to the ending. And, at least the final scene...well, it worked VERY well and gave me exactly what I wanted!