"Colleen" definitely is a silly story, as other reviewers have noted. Such comedies work as comedy when they are really funny. That usually means clever, witty or outlandish dialog; or great antics or situations; or combinations thereof.
Unfortunately, this film has just a few spurts of comedy, mostly in the dialog. It's musical part is moderately good. The film has a good cast for the period. Dick Powell, Ruby Keeler, Joan Blondell, Hugh Herbert and Jack Oakie.
Ruby Keeler doesn't have a good singing voice at all. She even said that she dreaded it when she had to sing. So, one wonders why Warner Brothers had her sing at all. She was very good as a tap dancer.
Paul Draper does some excellent tap dancing as Paul Gordon. This was his first of just two films he made. Much of his career was on Broadway where he danced and choreographed shows. The fashion dance scene is a bit of an extravaganza but even it couldn't compare to those lavish productions by Busby Berkley at MGM.
Here are the funniest lines in this film.
Cedric Ames, "You know, all my life, I've wanted to have a hat and a cane just like this." Joe Cork, "All my life I've always wanted to have a boss just like you."
Logan, "Anything can happen to Mr. Ames if he's left alone with anyone for some time."
Logan, "I'm afraid your uncle has delusions of becoming a business executive again. We must find something for him to do." Donald Ames, "Well, I'll try to talk him into going around the world as soon as I get back from Chicago." Logan, "Yeah, but it's such a small world."
Logan, "What can we get him to do that would be harmless?" Donald Ames, "Have him cut out paper dolls." Logan, "Ah, he'd cut his fingers off." Donald, "Give him a pair of boxing gloves - no, you better not do that. He might knock himself out."
Minnie, 'Did you girls see anything of that book I was reading this noon?" Lois (uncredited), "What's the name of it, Minnie?" Minnie, "I don't know. It had a yellow back with a picture of a girl stabbin' herself on it."
Mabel, "Oh, please, Mr. Ames, have another one. I work on commission, you know. And everything I get goes toward my tonsils."
Colleen, after a knock on their door, "See who it is, pop." Pop Reilly, "I regret to say I am busy."
Minnie Hawkins, "His biography? Oh, I've always wanted to write one. Can I help?" Joe Cork, "Fair enough. I'll take you to a swell chop suey parlor where they've got a pen." Minnie, "Oh, swell."
Donald Ames, "Minnie, you've never been abroad, have you?" Minnie, "See here." Donald, "Oh, I mean Europe, Paris, London."
Colleen, "What you need is some beefsteak for that eye." Donald, "Oh, that's just propaganda put out by the meat packers so they can sell more beef." Colleen, "Come on, you're not gonna tell a Reilly how to cure a black eye?"
Donald, "Tell the lady he's in a coma. He's been in one for four years."