Marcus and Kevin Copeland (played by Marlon and Shawn Wayans, respectively) are brothers and FBI agents. After botching an undercover operation, they are saddled with the task of babysitting socialites Brittany and Tiffany Wilson, who are the targets of a kidnapping scheme. After a car accident leaves the girls with a few minor scratches that they consider disfiguring facial wounds, they refuse to go to their planned destination in the Hamptons, where a major FBI operation is covertly being set up to protect the girls and oust the kidnapper. Not wanting to lose their jobs, Marcus and Kevin decide their only option is to go undercover as the Wilson sisters. Hilarity Ensues.
This film provides examples of the following tropes:
- Abhorrent Admirer: Latrell is this to "Tiffany", in his typical Scary Black Man persona.
- Affectionate Parody: Of Some Like It Hot, only with more lampooning socialites, Terry Crews, and "your mama" jokes.
- Alpha Bitch: The Wilson twins, though they're more ditzy than type.
- Their rivals the Vandergeld sisters, Heather and Megan, play this straight.
- Ambiguously Bi: Latrell. He drunkenly has sex with Russ, believing him to be Tiffany. Also, when he learns that "Tiffany" is really a man, he's horrified but mainly because he's black.
- Am I Just a Toy to You?: Right before the climax at the fashion show, Karen, a the insistence of Tiffany/Marcus decides to tell Heath that she's through being his "late night booty call," and breaks it off with him saying that he's happy to string her along while claiming that they'll begin dating soon as he dumps Megan.
- Attractive Bent-Gender: When Marcus and Kevin disguise themselves as the Wilson twins, Latrell starts flirting with Marcus throughout the film.
- Bedmate Reveal: Latrell wakes up to find that he is sharing his bed with Russ.
- Boomerang Bigot: Latrell, who is more shocked at the reveal that Tiffany!Marcus is a man of color rather than being a man dressed in disguise. Which is ironic considering Latrell is also a man of color.
- Clingy Jealous Girl: Marcus' Wife, Gina. She even showed signs of this before Marcus went off on the case.
- Comically Missing the Point: After Latrell gets shot, his right-hand man goes over to him and whips out a handkerchief, going "Don't worry, we'll get this stain right out." And again, his reaction after finding out that Tiffany is a guy.
- Dance Off: One that's intentionally not that impressive, as it's between two groups of WASP girls, but Serious Business all the same. Karen, Lisa, and Tori almost lose until the "Wilsons" step in and win it for them.
- Different for Girls: The Copelands constantly fumble with playing the part of white valley girls, but no one seriously picks up on any of the oddities.
- Disguised in Drag: The Copeland brothers disguise themselves as the Wilson sisters in order to complete their mission.
- Enemies Equals Greatness: Russ' quote:"Don't hate me 'cause you ain't me!"
- Explain, Explain... Oh, Crap!: The Wilsons read the paper of "their" success on The Hamptons, but then remember they weren't actually at the event but were in their New York hotel room the entire time, thus realizing the the Copelands' were impersonating them.Tiffany: Oh, my God! Brittany!
Tiffany: We're on page 6!
Tiffany: Yeah! Look! (shows the headline) "Wilson Sisters Rock Hamptons"!
Brittany: Wilson sisters rock!
Brittany: Wait a minute... We weren't in The Hamptons this weekend!
Both: OH, NO! WE'VE BEEN CLONED!
- Fun with Acronyms: The benefit dinner is called the Southampton Nuclear Opposition Benefit.
- Gender-Bender Friendship: While disguised as the Wilson twins, Marcus and Kevin start hanging out with the sisters' best friends Tori Karen and Lisa. And even the truth came out, the girls find that they liked the Wilson sisters much better when Kevin and Marcus were them. The girls and the Copelands agree to keep in touch and go shopping together.
- Growling Gut: Marcus (disguised as Tiffany) eats a whole tray of cheese appetizers. However, he's lactose intolerant, so the appetizers cause his stomach to growl due to a need to use the bathroom.
- Henpecked Husband: Marcus, whose wife flies off into a jealous rage for even the smallest discrepancies; it's Played for Laughs.
- Heroic Sacrifice: Latrell towards Marcus!Tiffany. He got better since he survived the shot.
- I Have Boobs, You Must Obey!: Megan tries seducing the director of the fashion show runway. Unfortunately for her, it doesn't take. "Oh, Honey, you are so barking up the wrong tree right now".
- If It's You, It's Okay: Latrell's indifferent reaction to Tiffany!Marcus admitting she's not who he believes she is. He's rather much more shocked at the reveal that Tiffany!Marcus is black and not even caring that he's a man.
- Incredibly Conspicuous Drag: The Wayans brothers still look like two black men, but the disguise seems to fool everyone. Shawn Wayans himself admits to being a "very ugly woman" in the DVD Extras.
- Informed Attribute: In the finale, Marcus tells Gina about how wonderful a wife she is because of the kind things she does for him — but the audience only ever sees her as a Clingy Jealous Girl to her husband.
- Large Ham: Terry Crews as Latrell Spencer. Probably the funniest part of the movie.
- Larynx Dissonance: When the Copelands put on their "Wilson" voices, it always sounds just a little... off. Though when they drop to their normal speaking voices while in disguise, it's equally disconcerting.
- Meaningful Name: "Vandergeld" means "for the money" in Dutch.
- Minor Injury Overreaction: The Wilsons "suffer" some minor scrapes in a car accident, which snowballed into the main plot. Brittany and Tiffany just scream when they both see that the other has a scratched up nose and busted lip from the car accident
- Mistaken for an Imposter: When Gomez and Harper capture who they believe to be Kevin and Marcus disguised as supermodels Brittany and Tiffany, they forcibly undress them in front of their superior to prove it. Turns out they actually captured the real Brittany and Tiffany, who punch them unconscious in retaliation for the undressing.
- Mistaken for Cheating: Marcus' wife Gina thinks her husband is cheating on her when she sees him with "Brittany".
- Mistaken for Gay: When Marcus!Tiffany cheers up Karen and gives her a heartwarming talk about a special person being right in front of them. Karen asks if she's a lesbian.
- Mushroom Samba: Latrell suffers this after drinking the Ecstacy laced drink meant for "Tiffany" as he ends up dancing shirtless to techno music with glowsticks and a whistle. Then he accidentally ends up in bed with Russ.
- No Celebrities Were Harmed: Brittany and Tiffany Wilson, for Paris and Nicky Hilton.
- N-Word Privileges: Played for Laughs when the Copelands, in their disguises, listen to rap music in the car with the Wilsons' friends. The girls are horrified when the "Wilsons" say the n-word, until they explain that there's nobody around to hear them and that it's okay if it's in a song.
- Oh, Crap!: Russ has this reaction during a fight ("mama?"), when he smashes a chair over "Brittany's" head, to no effect whatsoever.
- When Marcus!Tiffany enjoys a plate of quiche only to find out they're filled with cheese and he's lactose intolerant.
- When Marcus' wife Gina shows up at the hotel looking for Marcus.
- Paper-Thin Disguise: Marcus and Kevin are, shall we say, not entirely convincing as white girls, to the point that it strains the Willing Suspension of Disbelief that none of the other characters suspect.
- Poisoned Chalice Switcheroo: Marcus pulls this on Latrell after he tries giving a ecstasy-laced drink to "her".
- Preferable Impersonator: Despite their Paper-Thin Disguise, Marcus and Kevin are much nicer than the real girls and are accepted.
- Sassy Black Woman: Gina is always ready with a retort and more than willing to get her claws out.
- Single-Target Sexuality: Latrell only has eyes for "Tiffany."
- The Stoner: "Party Boy" Russ, who enjoys slipping estacy into his date's drinks and getting high on estacy and coke.
- Twelfth Night Adventure: One of the oddest examples of the genre.
- Upper-Class Twit: The Wilsons, their Girl Posse, and the Vandergelds. Making fun of socialite culture is pretty much the point of the movie.
- What the Hell, Hero?: Both Copeland brothers. Their first mission ends up a failure for picking on the wrong gang, The FBI's two best agents get fired because of their crossdressing plan, and more. Fortunately, the brothers got better and saved the day.
- Where da White Women At?: Latrell, to the point that when Marcus reveals himself, Latrell gets more upset that he's black, without even acknowledging that he's a man.
- White Like Me: The entire plot involves two black guys dressing up to pass as, well, White Chicks.
- Wig, Dress, Accent: The Copelands don't look anything like the Wilsons, even in whiteface disguise, but the blonde wigs, feminine dress, and valley girl accents fool everyone.
- Your Mom: The Copelands pull this one off on the Vandergelds, who visibly struggle to keep up until their father arrives.