The basic premise of the film is this: Kevin Franklin (Sinbad), an unsuccessful 35-year-old man in living in Pittsburgh, tries to pull of a get-rich-quick scheme, using borrowed money from the mob to do so. Like all his other plans, it flops, so he tries to run for it when the mobsters come back for him. They catch up with him at the airport, whereupon he hears a man talking to his kids. The man, Gary Young (Hartman), is waiting for his childhood friend Derek Bond (Ron Glass), to visit him for the first time in 25 years. Young remarks that he doesn't know what Bond looks like now, except that he's black and in his thirties. Naturally, Franklin decides to pose as Bond and ends up spending a long weekend with them as their houseguest. All the while, he's trying to avoid the dim-witted mobsters sent after him while trying figure out exactly who he's supposed to be an impostor of in the first place. Hilarity Ensues, as you've probably guessed.
- The Alleged Car: Kevin at the beginning of the movie. He gets a nicer one at the end.
- Angry Guard Dog: The Young family's Doberman is a vicious and effective guard dog, even barking at Kevin, but the two eventually bond over food.
- Big Fancy House: The Youngs live in a nice-sized two-story home in the suburbs.
- Blatant Lies: When Kevin swipes a random suit at the airport luggage claim and joins Gary at a high-class function, the "GFH" (which is really the logo for a funeral home) on its lapel he lies and claims that it's various occupations and monograms, including "G-strings for the Huge", "Girls Feeding the Homeys", and "Graduated, Full Honours" (from University of Oxford).Random, annoyed man: I went to Harvard! (storms off)
Kevin: Yeah, Harvard Street!
- Butt-Monkey: Bond. Sure, he's kind of a jerk, but all he wanted to do was visit his childhood friend. And yet in his ten minutes of screen time, he gets beaten up, kidnapped, and called ugly.
- Covered in Gunge: A woman that Kevin tries to flirt with at Gary's party ends accidentally being splattered in creamer from a cappuccino maker.
- Disproportionate Retribution: One of Larry's former customers, a biker, is quite unhappy about the tattoo he was given. To show his displeasure, he not only crashes through Larry's parlor on his motorcycle to show off what a Harley-Davidson should look like, but also beats him up offscreen (as evidenced by Larry's later black eyes and busted lip).
- Dissimile: Kevin compares himself to Poseidon at once point. Larry responds that Poseidon is exactly like Kevin except that "he's white, he's Greek, and he's a god".
- DIY Dentistry: Referenced when Kevin, who is posing as a dentist, is called upon to actually perform a tooth extraction.Dr. Timmerman: Horizontal fracture with a periapical infection, and pulpal necrosis. He needs a root amputation to avoid periodontal trauma. I'd administer 7.2cc of xylocaine with epinephrine. But... What do you think?
Kevin: Let me see that, Doctor. Yeah, OK. That's better than tyin' a string to a doorknob and slammin' it shut.
- Drives Like Crazy: A lot of characters, but Kevin's terrible driving skills deserve special mention.
- Easily Forgiven:
- In spite of his understandable shock and initial disgust at learning that Gary was really Kevin and had conned him and his family, after Kevin apologizes to them before the mobsters abducted him, they all surmised what a great guy he was and all that he did with and for the family.
- Averted with Brooke's (ex-)boyfriend, who after a scary encounter with Kevin where he led him to believe that he was going to be hit by a train, he begs for her forgiveness, only for her to rebuff him.
- The Family for the Whole Family: Could the mobsters possibly be any stupider? Even the mob boss calls them out on their incompetence after they repeatedly fail to capture Franklin.
- Food Slap: Gary gives his boss an epic one after deciding to stand up to him and quit, smearing yogurt in his face and calling him out on his assholery before hi-fiving Kevin.
- Goth: Brooke mostly fits the stereotype (dyed black hair, sour attitude, rebels against her parents, and a gloomy bedroom setting).
- Jerk with a Heart of Gold: Kevin starts the movie caring only about himself and what he wants, but after his time with the Youngs learns The Power of Friendship.
- Jerk With A Heart Of Jerk: Gary's boss, who at first just seems arrogant, but then is quickly revealed to have almost no morals (e.g. trying to get Gary to spy on his own wife's yogurt business to figure out how to destroy it).
- Laser-Guided Karma: The mobsters initially swipe Kevin's winning lottery ticket and go on a wheel spin to win a million dollars. While it does first land on the million, the bumbling crooks' jumping up and down cause the ball to fall down and land on a measly $500 instead, earning them being publicly humiliated and chewed out by their angry boss.
- Meat Versus Veggies: Discussed. While the real Dr. Derek Bond is a strict vegetarian and is a bit pretentious about it, Gary soon lampshades it to Kevin (then masquerading as Bond) about how he himself couldn't go without meat. Eventually, when the two are bonding on a bridge while the latter is eating McDonald's, Kevin bites into the burger, sobbing "I have weaknesses!" Instead of being angry or disgusted, Gary is relieved at him not being perfect, gives him the other burger he bought and even agrees to keep his secret.
- Nice Guy: Gary Young, who is not only a successful lawyer and loving (albeit initially distant) family man, but grows close to Kevin and even remains friends with him even after his true identity is exposed, namely because of what a charming guy Kevin is and all that he did for the family, including teaching Jason to play basketball, understanding Brooke's teenage angst, watching cartoons with Sarah and teaching Gary to stand up against his racist jerk of a boss (and in connection, protecting Emily's yogurt shop).
- Old Friend: Bond to Young. Odd in that though he thinks the trope is played straight (childhood friend comes to visit and turns life upside down), Bond only has a small part. The rest of it was just Franklin.
- The Power of Friendship: Kevin's interactions with the various members of the Young family allow him to stop behaving as a selfish conman and learn about honesty and how to be a true friend to others, including the family and Larry. At the end of the film, all of them are enjoying themselves at a Christmas party.
- Pretty Fly for a White Guy: Gary's daughter dates a stereotypical white gangster wannabe.
- Product Placement: McDonalds paid to be in the movie as Kevin's favorite place to eat (which causes issues when he finds out that Bond is a strict vegetarian). Since there's not a McDonalds in Sewickely, PA (where the movie is set), they actually dressed up a bagel shop as one just for this movie.
- Running Gag:
- Kevin can't park to save his life. Even at the end of the movie when he becomes rich and drives a nice car, he still can't park it without pushing aside adjacent cars.
- Gary and Kevin singing their old camp song, "O Mapleridge".
- When trying to cheer up Brooke, Kevin alludes to basketball player Charles Barkley and his popular Right Guard deodorant commercials at the time.
- In the closing credits, as Sinbad and Phil are singing improvised Christmas carols, the former at one point does his famous Bill Clinton impersonation from Saturday Night Live.
- "Shut Up!" Gunshot: When towards the climax of the film when the mobsters catch up to Kevin and holds the family hostage and they learn Kevin's real name, a still in denial Gary tries to disprove them by having them sing their camp song, "Ol' Mapleridge". Midway through singing, the main mobster shoots the son's basketball to get them to stop.
- Trapped by Gambling Debts: Not gambling per se, but Kevin's debt to the mob is what drives the plot.
- Two First Names: Kevin Franklin.
- Verbal Backspace: Done by Kevin when first meeting Gary, who believes him to be his long-lost friend Derek:Gary: How's your wife?
Kevin: My wife? (humbled) My wife is dead, Gary.
Gary: (shocked) She is?! I just spoke to her last week! She sounded fine!
Kevin: Oh! I meant, she's dead inside... (serious) about the loss of our son.
Gary: I thought he was attending Princeton!
Kevin: I meant...losing him...to an Ivy League school!
- Wouldn't Hurt a Child: For all of the mobsters (apparently) intimidating ways, they have no interest in harming children, even when warning Gary and Kevin, they tell the former to cooperate on the sake of his beautiful family.
- Your Television Hates You: After being slapped then dumped by his girlfriend, Kevin flips through several channels of people being slapped, including a young Homer Simpson and Sam and Diane.