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The series' main character, Jerri Blank (played by Amy Sedaris), was a runaway returning to high school as a freshman at age 46 at the fictional Flatpoint High School in the town of Flatpoint.

Created and written by Amy Sedaris, Paul Dinello, Stephen Colbert, and Mitch Rouse, the show was a spoof of the after school specials of the 1970s and 1980s and was also inspired, at least in part, by a 1970 public-service film, The Trip Back, that featured a reformed drug addict named Florrie Fisher (see "Origin" below). Sedaris, Colbert, Dinello, and Rouse were cast members of the short-lived Comedy Central series Exit 57; they, along with Greg Hollimon and many other stars of the series, were also alumni of Chicago's Second City comedy troupe.

According to the show's animated introduction, Jerri ran away from home and became "a boozer, a user, and a loser" after dropping out of high school as a teenager, supporting her drug habits through prostitution, stripping, and larceny. She has been to prison several times, the last time because she, in her words, "stole the TV."

Every episode featured a theme or moral lesson, although the lessons were often amoral or warped; in an episode about eating disorders, Jerri learns that it's OK to become an anorexic because it will get people to pay attention to you. When Jerri's father passes away in the episode "The Goodbye Guy," Jerri learns the valuable lesson, "You never really 'lose' your parents. Unless of course they die. Then they're gone forever. And nothing will bring them back." In another episode, Jerri learned that "violence really isn't the only way to resolve a conflict, but it's the only way to win it."

Each episode ends with the cast and other featured actors from the episode dancing.

The series was first envisioned by Dinello and Colbert, both of whom had seen a Scared Straight!' type public-service film called The Trip Back, in which motivational speaker Florrie Fisher recalled her days as a New York prostitute to a group of high-school students. Seeing that Fisher strongly resembled their friend Amy Sedaris, they showed her a copy of the tape and, suitably impressed with Sedaris's imitation of Fisher, began developing a series based around the idea of Fisher going back to high school herself. The three, along with Mitch Rouse, combined this concept with lampooning the after school specials they had all been subjected to in high school, along with the short-lived mid-1990s teen series My So-Called Life. Much of Jerri's past is taken from anecdotes in The Trip Back, some of which were also included in Fisher's autobiography, The Lonely Trip Back. Several lines of dialog in the series were taken verbatim from Fisher's public-service film.

It is arguable that Jerri Blank has become even more famous than the woman that inspired her; while Strangers with Candy became a cult success, Florrie Fisher sank into obscurity in the 1980s. Today, much speculation among fans of the series revolves around finding out whatever happened to Fisher.

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