Junior identifies himself to Sugar as heir to the Shell Oil Company. However, Shell Oil had no presence in North America at the time the story takes place; its first U.S. distributorship opened in December 1929 in North Carolina.
One of the goons searching for Joe and Jerry assures the other goons that his men have the airports covered. Miami had just one airport at that time, Pan American Field, which consisted of a single hangar and served just one route, Miami-Havana.
Early in the movie, Joe says, "Maybe the Dodgers will leave Brooklyn," which is of course funny because the movie came out in 1959, one year after the Dodgers moved to L.A. But the movie is set in 1929, and from 1914 to 1931 the Brooklyn baseball team was known as the Robins, not the Dodgers.
Although rim brakes (those on Junior's bicycle) have been in use since the 1890s, the vast majority of early 20th century American bicycles used coaster brakes. In real life, Junior would have been hard-pressed to find a bike with rim brakes.
The trumpet solo during "I Wanna Be Loved by You" is heard even though the trumpet player behind Daphne and Josephine is not playing her instrument. At one point in the same song, Daphne plays the bass, but the bass isn't heard.
As Sugar sings "I Wanna Be Loved By You" there's an extended shot of her with the drummer, a bit out-of-focus in the rear, and the drummer is clearly "missing" the drum and cymbal by a wide margin with her brushes.
Mulligan asks for another table not so close to the band and refers to the reserved table. However, we can see in the next shot that the reserved table is right next to the stage and therefore just as close to the band as he is.
Joe as Junior leaves the hotel by stepping out his window, then walking to his left on the terrace to climb down a pole. When he returns, he climbs over the terrace railing into the window instead of walking on the terrace (after, presumably, climbing up the pole).
Osgood tells Daphne that his mother sent him to Florida when the yearly "George White Scandals" opened. The film is set in February; the "Scandals" never opened earlier than June, and the 1929 revue opened in September.
While she chops at the ice, Sugar straightens up when she tells Josephine about her weakness for saxophone players. When we cut over her shoulder to see Josephine's reaction, Sugar straightens up again.
As Daphne dumps her things onto Osgood, his hand is grasping the top of Josephine's saxophone case, the neck of Sugar's ukulele case is pointed away from him while Daphne's purse is stuck between him and Josephine's case. But, when they enter the lobby, Osgood's arm is now under Josephine's case, the neck of Sugar's case is pointed toward him, and Daphne's purse is between Josephine's case and Sugar's case.
When Osgood puts Daphne's shoe on, the luggage on the sidewalk behind him is in a straight line. When we cut back to Osgood, the luggage is no longer in a straight line, and other luggage is stacked on top of it.
In the opening, four hoodlums are riding in the hearse and they hear a police siren behind them. Two of them look out the back window and it is apparent that there is no glass in the window. A second later a bullet smashes the window and, when they look out again, the window is not only broken, but very dirty.
After the back window of the hearse is shot by the police, the two thugs knock out the rest of the window with their guns to shoot back, leaving pieces of glass on the bottom frame. But, the next time we see the hearse, the pieces of glass are gone.
When we first see Sugar, we notice the seams of her stockings run a straight line up the middle of her calves. But, when she asks Daphne and Josephine a few minutes later if her seams are straight, they are no longer in a straight line nor up the middle of her calves.
After Sugar performs "I Wanna Be Loved by You," we see her back is bare as she turns away from us. When she boards Junior's boat, there is now a transparent strap across her back joining her dress. When she enters the salon moments later, the strap is gone.
When Joe and Jerry arrive at Poliakoff's building, Joe's hair is wind-blown with snow in it, and he has stubble on his face. But, when they are in the building, Joe's hair is combed with no snow in it and he's clean-shaven.
Poliakoff's cigarette is one-quarter burned when Sweet Sue and Beinstock leave his office. Moments after Joe and Jerry enter his office, Poliakoff's cigarette is almost down to the stub. When Joe and Jerry are about to leave, Poliakoff's cigarette is half-burned.
At the speakeasy, a lady at a table to Mulligan's left gets up and begins to walk in front of the chorus girls just as we cut to Spats entering. The lady should be now seen in front of Spats, but isn't.
When Spats and his crew go to their table at the speakeasy, the henchman played by Harry Wilson sits at the table directly across from Spats. When Det. Mulligan goes to the table to confront Spats minutes later, Wilson is sitting to the right of Spats.
As Daphne and Osgood are going into the hotel, when the camera is outside the hotel Daphne is holding her right wrist up and moving her left arm forwards and backwards. When the camera is inside the hotel, her left wrist is elevated (not as high as the right wrist was) and her right arm is moving.
When the bus carrying the band approaches the hotel, there is nobody on the bus but in the next shot, the band exits from the rear door. If people had been on the bus, they would have been easily visible from the side views.
In the speakeasy as we see Mulligan packing his cigar, the top of someone's head is in the bottom of the screen. However, in the scene where he first sits down at the table, you can see that there's no place for that person to be sitting as he is right next to the stage.
Florida beaches do not have high cliffs. Also, there is a scene where Sugar Kane is sitting on the beach, facing the ocean. She says that the time is 4:00 pm. However, her shadow is clearly being cast behind her. On Miami beaches, this is not possible. Since all of Miami's beaches face east, one's shadow is only cast away from the ocean before noon. On Miami beaches at 4pm, your shadow would lie on the ground in front of you, towards the ocean.
The depiction of the St. Valentine's Day Massacre is deliberately inaccurate, to spoof Scarface (1932) and other classic gang movies which sensationalized and fictionalized real people (including Al Capone) and events. It's a comedy, not a documentary. To be specific, the shooting took place at mid-morning, not at night. The hitmen did not drive into the garage as shown; they parked outside. They drove a Cadillac, not a Duesenberg Model J as in the movie, and two of the four actual killers were dressed as policemen.
During the chase, the lid of the coffin is leaking fluid from bullet holes which would indicate that the coffin is very full. When the lid is raised, no liquid pours out and only broken bottles are seen.