Penthouse from 1933 with Warren Baxter, Myrna Loy, Charles Butterworth and Nat Pendleton
This pre-code-on-steroids story is a bit sloppy and obvious in its plotting, but makes up for it in its aggressive reveal of the grey areas of life that, in only a year, with the coming enforcement of the Motion Picture Production Code, would be mostly hidden from view in movies for several decades.
But before that window closed, in Penthouse, Warren Baxter played a white-shoe lawyer who gets a mob boss, Pendleton, off on a murder rap, but is then dropped by both his law firm and society fiance who disapproved of Baxter's "association" with criminals. Baxter, bored with writing wills for wealthy old ladies, continues in his new career path, even socializing with Pendleton.
When he tells Pendleton of his romantic travails, Pendleton offers him one of the young women, in this case, Myrna Loy, who are, effectively, kept mistresses of the racketeers or other wealthy men. Loy, clearly loving the role of a wanton woman, is more than happy to "entertain" Baxter and is shocked when, after a late evening that winds up at his penthouse, he lets her sleep over without making any advances - advances that she encouraged (you got to love the pre-codes).
Heck, taking it a step further, we see that Loy's pride is hurt by his behavior, as, the next morning, when he tells her she's alluring, she responds, "Alluring? I doubted it last night as I didn't exactly have to fight for my honor. A few more weeks of this and I'll be out a position." I guess you have to respect that she takes pride in her work. Kidding aside, it is a stark reveal of a woman who understands her role and what is expected of her. It's a shame that, in only a year, we'd no longer meet women like her in movies for several decades.
But with that set up, the movie ramps up all the tension and conflict when a young society man is charged with murdering his mistress. He was trying to break up with her - get ready for it - to marry the society woman who broke off her engagement with Baxter when he became a lawyer for the mob. So now, Baxter's ex-fiance comes to Baxter asking him to defend her new fiance. Are there no other good lawyers in Manhattan?
Thrown into this mix are rival gangs, one of which is using the society boy as a fall guy for, what was, a mob hit on his former mistress. From here, the rest of this short, fast movie is watching Baxter reveal the frame-up of the society boy while avoiding being killed by one of the gangs. Along the way, both his former society girlfriend and Loy try to help him, which shows that Loy is the one of the two women with character, grit and loyalty despite being, as she describes herself, not someone you can take into proper society.
The wrap up is fast and clean (spoiler alerts) as the society boy is proven innocent by Baxter, Baxter's mob-boss friend is killed (in a surprisingly bloody way - blood also being something that will disappear from the screen in only a year) and Baxter refuses Loy's offer to be his mistress, instead, asking her to be his wife. The message here is a good one that denounces "society's" hypocrisy and the underworld's crime and violence, while advocating for each individual - like former society lawyer Baxter and high-price call-girl Loy - to be judged on their character, not on their "social standing."
N.B. Look for Charles Butterworth in the role of Baxter's butler. While we cringe a bit today at the thought of a butler, it was honest employment that, as shown here, could oftentimes evolve into a friendship based on respect and affection. In Penthouse, Butterworth delivers a wonderfully understated performance as the guy on the sideline who sees all the nonsense while firing off the occasional subtle putdown, but he will also defend the good guys - Baxter and Loy - when necessary.