On December 14, 2007, 20th Century Studios, and FilmFlex released the first of four Alvin and The Chipmunk films. The first film was directed by Tim Hill and earned $361.3 million in the box office.
1. Alvin and The Chipmunks (2007)
The first film in the four movie franchise follows Alvin (Ross Bagdasarian Jr. and Justin Long) , Simon (Matthew Gray Gubler and Steve Vining), and Theodore (Janice Karman and Jesse McCartney) after the tree they called home is cut down and shipped to a Los Angeles music studio. The talking chipmunks then find a new home with songwriter Dave Seville ( played by Jason Lee) while trying to escape the music studio in a muffin basket. "Despite a rocky start to this new arrangement, Dave eventually discovers that the spunky critters have rare singing talent. [Dave then creates a Christmas song.] When the three perform in front of record executive Ian Hawke (played by David Cross), he immediately signs them. Although the infectious group rapidly gains in popularity, their loyalty is soon tested."
The film also features Cameron Richardson as Claire, Dave's love interest. Jane Lynch also plays the role of Gail, Dave's boss.
During this film Theodore gained his popularity for his green eyes, green shirt, and cute/sweet personality. Simon gained a reputation for blue eyes, blue shirt, glasses, and his very smart personality. Alvin gained his very popular rep for the color red, the big "A" on his shirt, and his over the top/big personality.
2. Alvin and The Chipmunks The Squeakquel (2009)
Following the success of the 2007 film, 20th Century Studios came out with the "squeakquel" to Alvin and The Chipmunks 2 years later. The film released on December 11th, 2009, and made $443.1 million in the box office. Betty Thomas directed the film and David Newman did the music for the film.
"Now in the care of Dave Seville's nephew (Zachary Levi), chipmunks Alvin, Simon and Theodore take a break from pop-music stardom and return to school. Almost immediately, the tiny tunesmiths get the giant task of saving their school's music program by winning a battle-of-the-bands contest. Though the boys think winning it will be easy, romantic and musical sparks fly when they meet Brittany (Christina Applegate), Eleanor (Amy Poehler) and Jeannette (Anne Faris) -- also known as The Chipettes."
The film also stars Chris Warren Jr. as Zander, Bridgit Mendler as Becca, Wendie Malick as Dr. Rubin, Anjelah Johnson as Julie, Kevin G. Schmidt as Ryan, and Kathryn Joosten as Aunt Jackie.
3. Alvin and The Chipmunks Chipwrecked (2011)
December 16th, 2011 brought the world the third installment of the Chipmunk franchise. The film was directed by Mike Mitchell, and earned $342.7 million in the box office. The film follows "Dave Seville (Jason Lee), the Chipmunks (Justin Long, Matthew Gray Gubler, Jesse McCartney) and the Chipettes [who] are taking a luxury cruise to the International Music Awards. Of course, Alvin cannot resist the urge to create havoc, and the singing rodents soon find themselves marooned on a seemingly deserted island. While Dave and an unlikely ally launch a search, Alvin and company discover that they are not alone on the island, as they first thought." The movie also features Jenny Slate as Zoe.
4. Alvin and The Chipmunks: The Road Chip (2015)
The fourth and final installment of the franchise was released on December 12th, 2015. The film earned $234.8 million in the box office, and was directed by Walt Becker. This film follows, "Music manager Dave (Jason Lee) is not only enjoying a burgeoning career, but a blossoming romance with Samantha (Kimberly Williams-Paisley), a beautiful doctor who works in the emergency room. Through a series of misunderstandings, the chipmunks start to believe that a marriage proposal is on the horizon. Dreading the thought of an antagonistic stepbrother (Josh Green), Alvin, Theodore and Simon embark on a cross-country odyssey to prevent their best pal from ruining their lives." The film ends with Dave adopting the Chipmunks.
"Road Chip" also features Bella Thorne as Ashley Grey, Tony Hale as Benson, and Josh Green as Miles.
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