Jason Lee — who played the chipmunk’s mentor and guardian Dave Seville in the first film — is barely on-screen in The Squeakquel, laid up by calamity while the boys are on-tour in France; guardianship of the chipmunks, and the moral lessons that come with it, pass to Zachary Levi’s Toby. Toby is a little spacey and distracted (he’s a video-game nut), so he’s not exactly ready when the three mammals in his care not only have to deal with the blows and buffets of high school (you may ask why three six-inch talking chipmunks jump ahead to high school instead of a less dangerous environment, but if you start asking one logical question about The Squeakquel, so many of them soon pile up in your mind that your head explodes) but also with the arrival of three singing female chipmunks, the Chipettes, who are not only enrolled at the same school but also singers, managed by the nemesis of the first film, slimy music manager Ian Hart (David Cross).
A brief note about what may be the most enjoyable thing about The Squeakquel, which is not necessarily Cross’ performance but, rather, the way Cross and his role comprise a heated, fairly obvious ballet of hate between the film’s makers and himself. Cross apparently did not like being in the first film, and noted early on in production on The Squeakquel that while he was contractually obligated to be in the second film, he was not contractually obligated to be sober when his scenes were shot. This must have been seen as a challenge by the writers and director Betty Thomas, who continually humiliate and mock Cross and his character through a series of scenes that get worse and worse. It’s like Cross was determined to sleepwalk through any sequel and the people making it decided to slap him awake, and watching that moviemaking misery play out on-screen gives The Squeakquel its only jolt of real life.