Strangers with Candy (1999)

The cult Comedy Central series follows Geraldine Antonia “Jerri” Blank (Amy Sedaris), an ex-junkie/slut/runaway exiting jail and returning to high school as a forty-six year old freshman at the fictional Flatpoint High. Embodying the feel of an after-school special, the goofy show captures Jerri’s transition from lock up to navigating the mean-spirited hallways of her old high school, dealing with odd encounters with Principal Oynx Blackman (Greg Hollimon), and her goofy educators like history teacher Chuck Noblet (Stephen Colbert), art teacher Geoffrey Jellineck (Paul Dinello), and gym coach Wolf (Sarah Thyre). Life at home isn’t any better for Jerri, especially considering that she’s dealing with a catatonic father (Roberto Gari), a surly younger half-brother (Larc Spies), and an antagonistic stepmother (Deborah Rush). But all of Jerri’s miseries lead to pure laughter for us. Though there are more laughs than moments of skin, on season one, episode four, Stephen Colbert strikes a pose as a nude model, teasing a look at his clothes-less body and his butt crack as he gets up to wrap a towel around himself. Now that’s a piece of candy that everyone wants!