One of Robert Montgomery's most amusing films which takes a very serious turn is The Earl Of Chicago. Just imagine someone like a Lucky Luciano inheriting some title in Italy and you've got the basic idea.
For those who think Montgomery was miscast I disagree completely. He certainly had an upper class background and most of his film roles were of that kind, but he did just fine as blue collar types in Yellow Jack and Here Comes Mr. Jordan and he does equally well here.
What Robert Kilmont, Chicago gangster who hasn't let up a bit even though Prohibtion is a thing of the past, has is one great deal of hubris and he's an awful bad judge of character. He's right at the prison door to meet Edward Arnold, a lawyer he framed when he couldn't buy him. He reasons like Diogenes he's found an honest man and he wants honest men working for him. What's so ironic is that the whole audience knows from the git-go that Arnold is going to pull a double-cross even though Montgomery is oblivious to it all.
The opportunity comes sooner than he thinks when some English barrister comes across with documentation that shows this man who was raised in a Detroit orphanage is indeed the new Earl of Gorley. Montgomery is used to dealing with all kinds of situations, but this one throws him. He takes his new found friend Arnold to the United Kingdom to claim his inheritance. As for Arnold, he may be a disbarred attorney, but he knows what to do with a power of attorney which he tricks Montgomery into giving him so he can watch his business interests in Chicago from Great Britain of course.
It's a dirty double-dealing trick Arnold plays, but Montgomery was such a fathead to think this guy was going to just let bygones be bygones. That's the hubris.
Montgomery is in for quite a bit of culture shock about Great Britain and its class system and the fact as a member of the landed aristocracy he has traditions and obligations to follow and meet. The only real friends he makes among the folks there are young Ronald Sinclair who would be his successor and his butler Edmund Gwenn who tries in his usual gentle manner to smooth some of the rough edges that Chicago left on Montgomery.
In fact Gwenn's is the best performance in the film. It's certainly one my favorites from this player. I like it even better than his scientist in Them or as Kris Kringle in Miracle On 34th Street for which Gwenn won an Oscar.
Arnold's double-dealing ends badly for both him and Montgomery, but I will say in the end The Earl Of Chicago went out with the class he sought all of his life. And The Earl Of Chicago courtesy of Robert Montgomery and Edward Arnold and a number of players from the British colony in Hollywood make it a film of class.