He's left all kinds of businesses to his daughter, including a nightclub that Taylor runs. The rest of the gang consists of such various types of Hollywood villainy as Henry Kolker, Russell Hopton, Raymond Hatton, and Jack LaRue. The idea is for these guys to low ball the success and future prospects, get Bruce to sell to them and then turn around and sell the whole package to a rival promoter. Taylor's job is to romance Bruce which he undertakes and that of course is not seen in a good light by his girlfriend, Helen Twelvetrees.
The romance angle was easy for Taylor as he and Virginia Bruce were involved at the time. Virginia Bruce was in the process of getting divorced from John Gilbert when she and Taylor were kanoodling. Taylor does a fine job in the role, that major stardom was in his future was not even questioned.
But more than a big step up in Robert Taylor's career, Times Square Lady is the film in the song The Object Of My Affection was introduced by Pinky Tomlin who also wrote part of the lyric. This is an enduring classic, still as popular today as it was back then. Why it wasn't nominated in that second year of the Best Song category is a mystery.
A key film in the rise of a great career and an enduring popular song, most films don't have either of those things to their credit.