Jack Benny had a spectacularly successful career as a comedian, but just once in a while he showed some hints of real talent as an actor. The most obvious example is his starring role in 'To Be or Not to Be', but 'A Broadway Romeo' deserves attention too. Benny starred in this short film early in his career, when his comedic character as the egotistical tightwad (permanently age 39) was still gestating. (When he made this movie, he wasn't 39 yet!)
SLIGHT SPOILERS. 'A Broadway Romeo' takes place in the Times Square district of Manhattan, during what's clearly the Depression: everyone in the film (except ingenue Estelle Brody) is cynical and selfish. Jack uses an old confidence trick to cadge a free lunch for himself at a lunch counter: as he gets up to leave, he offers to pay for the lunch of the man sitting next to him (a total stranger), telling the man to look up and wave when Jack goes over to the cashier at the other end of the lunchroom, so that the cashier will know that this man's lunch is on Jack's tab. Of course, when Jack gets to the cashpoint, he tells the cashier that his **own** lunch is on the **other** man's tab, and sure enough the stranger looks up and waves at the cashier as if agreeing to this. Apparently, movie audiences in 1931 (hard hit by the Depression) were meant to admire Jack's resourcefulness in this scam.
Jack Benny's performance in this movie is a revelation, and much subtler than his usual comedy. After meeting small-town girl Estelle (alone in the big city after her fiancé just dumped her), Jack takes her under his wing. We can tell that he's on the make, but he also seems genuinely concerned for her welfare and sincere in his wish to protect her ... from everyone but himself.
There's a running gag that isn't funny, and has an obvious payoff. Periodically, a man walks past Jack and Estelle -- a different man each time -- waving hello, while Jack explains: 'That's one of my uncles.' The last man to do this is very effeminate, and Jack's punchline is visible from a mile off: 'My aunt.'
I'll rate this movie 6 out of 10, for an unusual look at a giant of comedy still finding his way.