Dumb and Dumberer: When Harry Met Lloyd (2003)

After years of homeschooling, dim-bulb teen Harry Dunne (Derek Richardson) finally makes the leap to public school and meets the equally intellectually challenged Lloyd Christmas (Eric Christian Olsen). The duo land in a "special needs" class created by Principal Collins (Eugene Levy) in order to bilk money from parents to fund his condo in Waikiki, Hawaii. His corruption is discovered by Jessica (Rachel Nichols), a fellow student who asks Harry and Lloyd to help her prove Collins' guilt.