Years after the film's release, a movie reviewer asked Tony Curtis why his "Josephine" was so much more feminine than Jack Lemmon's "Daphne." Curtis explained he was so scared to be playing a woman (or a man pretending to be one) that his tightly wound body language could be read as demure and shy, traditionally feminine traits, whereas Lemmon, who was completely unbothered, and "ran out of his dressing room screaming like the Queen of the May," kept much more of his masculine body language.

Jack Lemmon wrote that the first sneak preview had a bad reaction with many audience walkouts. Many studio personnel and agents offered advice to Billy Wilder on what scenes to reshoot, add and cut. Lemmon asked Wilder what he was going to do. Wilder responded: "Why, nothing. This is a very funny movie and I believe in it just as it is. Maybe this is the wrong neighborhood in which to have shown it. At any rate, I don't panic over one preview. It's a hell of a movie." Wilder held the next preview in the Westwood section of Los Angeles, and the audience stood up and cheered.

Tony Curtis has said that he asked Billy Wilder if he could imitate Cary Grant for his stint as the millionaire in the movie. Wilder liked it and they shot it that way. Apparently, Grant saw the parody of himself and stated, jokingly, "I don't talk like that."

When Tony Curtis and Jack Lemmon first put on the female makeup and costumes, they walked around the Goldwyn Studios lot to see if they could "pass" as women. Then they tried using mirrors in public ladies rooms to fix their makeup, and when none of the women using it complained, they knew they could be convincing as women. There is a scene on the train recreating this moment.

Marilyn Monroe wanted the movie to be shot in color (her contract stipulated that all her films were to be in color), but Billy Wilder convinced her to let it be shot in black and white when costume tests revealed that the makeup that Tony Curtis and Jack Lemmon wore gave their faces a green tinge.

Continuity

When the patrol car chasing the hearse is spun around, two cops are holding onto its right side. When it comes to a stop, one of the cops is in the back seat getting out.

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.

The pavement Sugar runs on from the hotel on her way to their pier is wet, but the pavement Junior rides his bicycle on from the hotel on his way to their pier is dry.

When the casket containing bootleg whiskey is shown in the hearse, it has two handles on the side. When it is shown being carried into the mortuary, it has three handles on the side.

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 the hearse arrives at the funeral parlor, the pieces of glass are back on the bottom frame.



Factual errors

In real life, the band would have boarded the Dixie Flyer, which ran from Chicago and St. Louis via Evansville, Nashville, and Atlanta to Jacksonville and Miami, not the "Florida Limited". The Dixie Flyer was still in operation when the film was made.

The bullets that fall out of Spats' gangster's pants are too large to fit his handgun. He has an automatic and the bullets are for a revolver.

Nellie's license plate is incorrect. Two groups of three numbers are separated by a dash on the actual 1929 plate, not one group of two numbers then a second group of three numbers. Also, the second "L" in the abbreviation of Illinois is dropped a half-space below the "I" and the second "L" and all three letters are capitalized. On Nellie's plate, Illinois is abbreviated as "Ill" in a straight line followed by a ".

Osgood tells Daphne that "Ma-Ma" sent him to Florida when George White's Scandals opened. The film is set in February 1929. The 1929 Scandals opened on September 23. The yearly revue (1919-1939) never opened sooner than June.

The sign as they approach the dock that says "Boats" is backwards. It should read "staoB"; instead it is reversed.



Incorrectly regarded as goofs

Early in the movie, Joe talks about the Brooklyn Dodgers, a name not officially used until 1932. From 1914 to 1931 the Brooklyn baseball team was the Robins, not the Dodgers. However, the Dodgers had been an unofficial nickname since 1895, and the World Series program from 1920 even referred to them as the Dodgers instead of the Robins.

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.

When Spats enters the Seminole, the hotel's name at the floor is readable from the lobby instead from the outside. The lettering should face towards the entrance, not the exit. This was intentional on the part of the filmmakers so that audiences wouldn't be forced to read "The Seminole-Ritz Hotel" upside down.



Revealing mistakes

The holes in the jacket of Jerry's bass do not correspond to the bullet holes in the bass.

When Spats' men are searched for weapons at the Hotel, the man doing the pat-down can be seen placing the gun behind the gangster's leg, just before it is supposed to drop out of his pants leg.

Obvious male stunt double for Sugar riding the bicycle down the stairs of the pier.

When Joe and Sugar arrive at the boat dock for their first date a neon sign is above the gateway. However it's facing the wrong direction: out to sea instead of towards the beach and hotel.

When Sugar and Junior are talking on the telephone, Sugar's eyes are clearly following lines on a cue-card.



Anachronisms

Osgood makes a ship-to-shore phone call using a Hallicrafters Model S-20R which came out in 1939. Also this radio is only a receiver and not a two-way radio.

Set in 1929, yet features the 1930s songs "I'm Thru With Love" and "Stairway to the Stars".

When Junior asks Sugar where she learned how to kiss, she replied that she sold kisses for The Milk Fund, an entity founded in 1932.

Junior identifies himself to Sugar as heir to the Shell Oil Company, but this group's first U.S. distributorship opened in December 1929 in North Carolina, after the movie takes place.

In Sugar Kane's introductory scene (the platform of the Chicago railroad station), her hairstyle, featuring spit curls, is at least a nod in the direction of the 1920s. The next time we see her (on the train, supposedly the same afternoon or evening of departure), her hairstyle is pure late 1950s.



Audio/visual unsynchronized

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.

During "I'm Thru With Love," a bass is heard even though Daphne is absent.

At the rehearsal and at the bandstand, Daphne's and the Sweet Sues' playing too often does not correspond to the notes of the music.

In the funeral-parlor-speakeasy scene, when Joe and Jerry stop playing and make their plans, the bass fiddle part appears to stop on the musical soundtrack as well, but when Jerry begins to hastily pack up his instrument to leave, the bass line can clearly be heard playing again on the songs soundtrack.



Crew or equipment visible

In the speakeasy as Mulligan packs his cigar, the top of someone's head is in the bottom of the screen. However, when he first sat down at the table, there was no place for anyone to be sitting as he is right next to the stage.



Errors in geography

When Sugar 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 band boards the train "Florida Limited" in Chicago. The Florida Limited was a companion to the Florida Special and both departed from Pennsylvania Station in New York. It never went near Chicago.

As the police chase the hearse, they pass a "Standard" gas station with the Chevron emblem. The Chevron emblem was used by Standard Oil of California only in the West. In Chicago, Standard stations carried the Torch and Oval emblem of Standard Oil of Indiana.

The Syncopators arrive in Florida and promptly check into the Hotel del Coronado in Coronado, California, a famous, unique, and easily recognizable Victorian structure.

The PA announcement at the Chicago train station lists the "Florida Limited" making its first stop in Washington and then stops down the East Coast. Trains from Chicago to Florida were routed through Nashville and other mid-South cities.



Plot holes

Jerry fits into the much-smaller Bellhop's uniform.

Joe and Jerry are so broke in Chicago that they have to hock their overcoats. Yet they are able to acquire an abundance of women's clothes and accessories.

The only information Joe has about Osgood's yacht is her name, so how does he know what The New Caledonia looks like, and where she and her motor launch are?

Joe fits into the shorter and stockier Beinstock's clothes perfectly.

Sugar could not have known where Joe and Jerry fled to after they left the hotel while being chased by the goons.



Character error

When Junior and Sugar return to shore after their night on the Caledonia, he does not tie up the launch to the dock. When Osgood returns to the launch seconds later, he makes no effort to untie it from the dock before he speeds off. He should have noticed that the launch has not been tied up. If the launch truly had not been tied up to the dock, it would have long drifted out into the open water.

At the speakeasy, Joe and Jerry continue to talk instead of resuming play with the rest of the band after the banjo solo ends.

Joe 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.

When Sugar tells Junior her band's name is Sweet Sue and Her Society Syncopators, he deduces that they play jazz, which she confirms. Although Joe (Junior) gets that impression from the rehearsal ("Runnin' Wild"), The Syncopators do not play jazz during their gig at the hotel.

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.