Remember the cult television classic Strangers with Candy, which ran on Comedy Central from 1999 to 2000? If so, then you’ll remember its star, the quirky-yet-lovable actress/comedian Amy Sedaris. Sedaris played Jerri Blank, a 40-something high-school dropout and recovering addict who re-enrolls at her erstwhile alma mater, Flatpoint High School.
Sedaris’s portrayal of the self-professed “boozer, loser, and user” was so unforgettable that viewers might have overlooked some of the famous faces she shared the screen with—including co-creator Stephen Colbert, who played Chuck Noblet, Jerri's history teacher. Here are 10 other well-known actors who also appeared on the (sadly) short-lived satire of after-school specials.
1. WILL FERRELL // "BOB WHITELY"
In “Trail of Tears" (Season 3 Episode 3), Jerri discovers she’s adopted—and that she’s Native American. Against her will, she's sent to a Native American-themed overnight camp to learn more about her heritage. There she meets the camp’s director, Bob Whitely, who's played by none other than Will Ferrell.
2. ELLEN POMPEO // "LIZZIE ABRAMS"
Long before she was cast as Dr. Meredith Grey on Grey’s Anatomy, Ellen Pompeo guest-starred on Strangers with Candy. The season one episode "Feather in the Storm" features Pompeo as Lizzie Abrams, Jerri’s rival on the school debate team.
3. PAUL RUDD // "BRENT BROOKS"
Equal parts bored and handsome, Brent Brooks is the most popular guy at Flatpoint High. He’s played by Paul Rudd in the series finale, “The Last Temptation of Blank.”
4. WINONA RYDER // "FRAN"
Winona Ryder has a knack for playing popular girls with steely exteriors and soft hearts. In “The Last Temptation of Blank,” she plays Fran, a mean classmate of Jerri’s who’s challenged with the task of making her awkward classmate cool enough to date the studly Brent Brooks. At the episode’s end, the aloof Fran admits her secret admiration for Jerri and resolves to change her ways.
5. DAVID CROSS // "DR. TREPANNING"
It’s difficult to think of David Cross without thinking of Tobias Fünke, but in season three's “Is My Daddy Crazy?” episode, he plays a physician named Dr. Trepanning who treats Jerri's surrogate father figure, Stew.
6. JANEANE GAROFALO // "CASSIE PINES"
It makes sense that Janeane Garofalo—who was a cast member on The Ben Stiller Show and now stars in Netflix's Wet Hot American Summer series—would make an appearance on Strangers with Candy. Garofalo plays Cassie Pines, a student counselor at Flatpoint High who speaks with a grief-stricken Jerri after her father dies in "The Goodbye Guy." She also returns for a brief appearance in “The Last Temptation of Blank.”
7. TIM MEADOWS // "PERCY KITTENS"
Mean Girls fans will remember Saturday Night Live alum Tim Meadows as Cady Heron’s high school principal. They may be less likely to recall his turn as a grief counselor named Percy Kittens, who visits Flatpoint High after someone commits a hate crime in the first season episode “Let Freedom Ring.”
8. CHERI OTERI // "HILLARY"
Another Saturday Night Live alum, Cheri Oteri plays Hillary, a member of Flatpoint High’s school board who turns the school into a strip mall during the show’s series finale. In turn, the school’s outraged principal urges Jerry and her classmates to burn down the building—an absurd yet fitting end to the show’s three-season run.
9. ANDY RICHTER // VARIOUS
Andy Richter had bit parts in three SWC episodes. In “Yes You Can’t,” he works at the artificial flower company in Jerri’s town. In “Trail of Tears,” he works at the Native American-themed summer camp that Jerri is forced to attend. And in “Blank Relay," he plays a pharmacy clerk.
10. HEATHER MATARAZZO // "RENEE"
Best known for her roles in Welcome to the Dollhouse and The Princess Diaries, Heather Matarazzo appears in season three's “Is My Daddy Crazy” as one of Jerri’s sleepover guests.