Billboard Girl (1932)
Bing is a magazine salesman on the road who falls in love with a college girl who is featured on billboards. Bing writes her letters, which are answered by her nelly brother. When Bing arrives at the college town, expecting a hot romance, the girl doesn't know him. The nelly brother than arranges a date with Bing. He is dressed in drag by his fraternity brothers, down to undies and stockings. The billboard girl witnesses Bing's impassioned wooing of her brother and wants it for herself. She takes her brother's place, myopic Bing being none the wiser, and swoons when Bing sings to her. Bing convinces the girl to elope with him. Her father objects. A wild Mack Sennett chase ensues. Bing wins out. The brother will have seek love elsewhere. One of the best of the Bing-Sennett two reelers.
Sing, Bing, Sing (1933)
Perhaps it goes without saying that Bing sings a lot in this short. In the opening scene he's at a radio station crooning "My Hideaway" into one of those massive, boxy microphones of the day. When he concludes, we learn that he and his girlfriend, Helen, are planning to elope. We learn this, along with all of Bing's listeners, because he simply addresses her at home, where she's listening to his broadcast, and unfolds the plan. Unfortunately for the lovers Helen's crabby father is listening also. He wants to marry his daughter off to a callow young man named Herbert, played by the one and only Franklin Pangborn, so it's no wonder Helen is keen to run off with somebody else. Bing shows up that night at Helen's home to whisk her away but Dad and Herbert are waiting, along with two detectives in standard issue derby hats. But Bing is unflappable, and when the elopement is thwarted he simply tries again in the morning. The runaways are pursued over a mountain highway in a zany car chase, but Bing and Helen win out in the end—and Bing, naturally, has time for one more song.
Blue of the Night (1933)
So the humor of this short is strained. Bing boards a train with Babe Kane and they find themselves sitting together. Everyone on the train is a honeymoon couple, and everyone suspects they are too. Ms Kane says she is not a honeymooner, but is engaged to the well known radio crooner Bing Crosby. Crosby never mentions his real identity. Later on an article appears in the newspaper regarding Kane's engagement to Crosby. This amuses her friends, mostly because it annoys Franklin Pangborn, who had said he was her fiancé (Kane tells him she never agreed to marry him).
Crosby reappears, and pretends for a moment to be a news reporter - then he reveals his real identity to Kane. But Pangborn thinks he is a phony. This leads to the idiotic final bet about the roadster against the five dollar bill from Crosby. Crosby's singing proves who he is.
Pangborn does several pratfalls into a swimming pool while in his fancy duds - a typical Sennett joke. Bud Jamison (who did better work with the Three Stooges) is a suspicious cop. The humor, for 1933, is infantile. But the singing and a look at a very young Crosby are worth seeing.