Winnie the Pooh and his friends (along with Ash, Bloom, Simba, Tai, and their friends) meet two unrelated young girls who happen to look identical and they suddenly meet. Amanda Lemmon is an orphan, and about to be adopted by a family whom she doesn't like, The Butkises. She actually wants her child-loving case worker Diane Barrows to adopt her instead. Diane would like the same thing but authorities will not let her, due to her low salary. Alyssa Callaway is coming home from her boarding school's piano recital competition, only to find that her wealthy father Roger is about to marry Clarice Kensington (whom Jafar, Maleficent, Myotismon, Dr. Facilier, Rothbart, Ursula, Morgana, The Grand Duke of Owls, Hades, Shan Yu, Scar, Shenzi, Banzai, Ed, Gaston, Hans, The Trix, The Crime Empire, and Team Rocket) a socialite who (secretly) hates kids and baseball (which Roger adores). The girls switch apples and find out that Diane and Roger would fit together perfectly. So they arrange "chance" meetings with the desired result: They fall in love with each other. After some turbulences, Alyssa who poses as Amy ends up being adopted by the Butkises. She and Diane (while looking for Alyssa) find out the only reason The Butkises have adopted many children were for the children to work in their salvage yard. When Clarice secretly spies on Roger and Diane, she decides to move up the wedding from the next month to the next day. After Amy, who poses as Alyssa, proves to Vincenzo who she really is at the church, he summons to have the real Alyssa picked up from the Butkises' salvage yard to stall the wedding. Once Diane and Alyssa end up at the church, Roger stops the wedding and tells Clarice that he fell in love with Diane. Furious, Clarice slaps Roger and prepares to do the same to both Amy and Alyssa but is stopped by both Diane and Vincenzo. Clarice storms out of the church, embarrassed. Roger and Diane both find out in the end that it was Amy and Alyssa that arranged all the meetings between the two of them the entire time.
- Ash Ketchum, Pikachu, Misty, Togepi, Brock, Bloom, Stella, Flora, Musa, Tecna, Layla, Simba, Nala, Timon, Pumbaa, The DigiDestined and their Digimon, Belle, Beast, Lumiere, Cogsworth, Mrs. Potts, Chip, The Penguins of Madagascar (Skipper, Kolwalski, Rico, and Private), Marlene, Princess Tiana, Prince Naveen, Louis, Ray the Firefly, Mama Odie, Aladdin, Princess Jasmine, Abu, Genie, Iago, Princess Odette, Prince Derek, Jean-Bob, Speed, Puffin, Ariel, Prince Eric, Flounder, Sebastian, Scuttle, King Triton, Princess Melody, Cinderella, Jaq and Gus, Snow White and the Seven Dwarfs, Princess Aurora, Prince Phillip, Flora, Fauna, and Merryweather, Mulan, Li Shang, Mushu, Cri-Kee, The Peanuts gang, Bob the Tomato, Larry the Cucumber, Junior Asparagus, Laura Carrot, Jimmy and Jerry Gourd, Pa Grape, Mr. Nezzer, Mr. Lunt, Archibald Asparagus, Jean-Claude and Phillipe, Madame Blueberry, Petunia Rhubarb, Alice, Hercules, Megara, Philoctetes, Pegasus, Pocahontas, Meeko, Flit, Princess Aurora, Peter Pan, Wendy Darling, Michael Darling, John Darling, Tinker Bell, Lucky, Cadpig, Rolly, Spot, Woody, Buzz Lightyear, Jessie, Rex, Hamm, Slinky Dog, Mr. Potato Head, Mrs. Potato Head, the Squeeze Toy Aliens, Bullseye, Dolly, Mr. Pricklepants, Buttercup, Trixie, Chuckles the Clown, The Teenage Mutant Ninja Turtles, The Smurfs (Papa Smurf, Smurfette, Gutsy Smurf, Brainy Smurf, Clumsy Smurf, and Grouchy Smurf), Boog and Elliot, Rodney Copperbottom, Cappy, Bigweld, Wonderbot, Fender Pinwheeler, Piper Pinwheeler, Lug, Diesel Springer, Crank Casey, Aunt Fanny, Dexter, DeeDee, I.M. Weasel, I.R. Babboon, Cow and Chicken, Mac Foster, Bloo, Coco, Wlit, Eduardo, Frankie Foster, Mr. Herriman, Felix the Cat, Lilo and Stitch and their friends, Scrooge McDuck, Huey, Dewey, Louie, Webby, Launchpad McQuack, Darkwing Duck, Bonkers D. Bobcat, Barney the Dinosaur, Baby Bop, BJ, Riff, Sofia the First, Princess Merida, Rapunzel and Flynn Rider, Princess Anna, Kristoff, Sven, Olaf, Elsa the Snow Queen, Jafar, Maleficent, Myotismon, Dr. Facilier, Rothbart, Ursula, Morgana, The Beagle Boys, Captain Hook, Mr. Smee, the Queen of Hearts, The Grand Duke of Owls, Hades, Scar, Shenzi, Banzai, Ed, Gaston, Prince Hans, Shan Yu, The Trix (Icy, Darcy, and Stormy), The Crime Empire (Joker, Harley Quinn, Two-Face, The Penguin, Negaduck, Megavolt, Quackerjack, Bushroot, and The Liquidator), and Team Rocket (Jessie, James, and Meowth) guest star in this film.
- Jafar, Maleficent, Myotismon, Dr. Facilier, Rothbart, Ursula, Morgana, The Beagle Boys, Captain Hook, Mr. Smee, the Queen of Hearts, The Grand Duke of Owls, Hades, Scar, Shenzi, Banzai, Ed, Gaston, Hans, Shan Yu, The Crime Empire, and Team Rocket will be working for the main villainess Clarice Kensington.
- This is an NTSC film with NTSC bits from the Winnie the Pooh films,the Pokémon films, Winx Club: The Secret of the Lost Kingdom, The Lion King films, Digimon: The Movie, the Beauty and the Beast films, The Princess and the Frog, the Aladdin films, The Swan Princess films, The Little Mermaid films, Sleeping Beauty, Mulan 1 and 2, Frozen, Hercules, and Rock-a=Doodle.
- Both the first three Pokémon movies and It Takes Two were released by Warner Bros.
- The Lion King was released on Home Video at the time when It Takes Two was released in Theaters in 1995 and the TV show The New Adventures of Winnie the Pooh was in reruns on ABC Satuday mornings.
- The only members of the Jungle Adventure crew to appear in this film are Simba, Nala, Timon, Pumbaa, Louis, Genie, and Sebastian.
- The only members of the Alfea Adventure Crew to appear in this film are Bloom, Stella, Flora, Musa, Tecna, Layla, Lumiere, Cogsworth, Mrs. Potts, Chip, and Scuttle.