I was just about to graduate from high school when Strangers With Candy premiered on Comedy Central in 1999. I’d never seen anything like it: The series, which was co-created by and starred Amy Sedaris and a pre-Report Stephen Colbert, was an absurd, over-the-top satire of after-school specials, PSAs, and Degrassi High. And, like most shows that are oddball and ahead of their time, it was not long for this world (only 30 episodes ever aired). Yet Strangers remains a fan favorite due to its sheer weirdness and Amy Sedaris’s all-in portrayal of Jerri Blank, one of the most disturbed, gross, and hilarious protagonists in the history of half-hour comedy.

Jerri is a 46-year-old freshman, a former high-school dropout who’s now the new kid at Flatpoint High. She desperately yearns to belong, but can’t help while standing out in every possible way, from her tacky makeup to her fanny pack. In the opening credits she identifies herself as “a boozer, a user, and a loser.” The character was inspired by a real woman named Florrie Fisher, the star of a PSA called “The Trip Back” in which she speaks to a group of high school kids, trying to set them straight with her hard-luck story. Fisher’s blunt delivery, outrageous quips, and purposeful style are all very much alive in Jerri, just taken to an extreme and tied up with a demented bow.

The thing that really makes Jerri Blank iconic, is Sedaris’s willingness to take the character as far as she can, unafraid to come across as reprehensible and downright ugly. She commits HARD, frowning and smiling with a rubbery expressiveness while sticking her teeth both out and sometimes slightly to the side at the same time. The clothes just add to the character, a creation both hysterical and horrific, a monster in mom jeans who is impossible not to love.

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Clockwise from top left:

Clockwise from top left: Levi’s denim vest, $78, Macy’s; bomber jacket, $20, Target; Make Up For Ever Technicolor Palette, $36, Sephora; earrings, $18, Macy’s

At first, I thought I would point out how wonderfully out of place Jerri’s outfits were: the crocheted tops, satin bomber jackets, ’80s costume jewelry, and turtleneck sweaters. Then I realized that, 13 years later, her penchant for high-waisted pants, floral patterns, and all things neon is totally “on trend,” which just adds another layer of genius to the series. Jerri would fit right in these days!

Or not. But she is always the first to go for any fad, whether it’s reclaiming her virginity, breaking into a store for a pair of Flairs (the sneakers with the extra-long laces that rich kids wear), or going back to her drug-addict ways in order to attract friends. And what I love most about Strangers is that she always seems to learn some kind of twisted lesson—even after she recognizes right from wrong, and then shamelessly exploits wrong to her advantage, Jerri lands on the vaguely moral side of things (mostly because she gets caught and has to own up to what she’s done). In the series finale, she gets a makeover from the coolest girl in school, played by Winona Ryder, and is forced to choose between being popular or being herself, and in the end, she makes the right decision, sort of. “I’d rather be unhappy and plain with average friends than be happy and beautiful with friends that are better than my old ones. I’m sorry, but that’s just the way I feel!”

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Clockwise from top left:

Clockwise from top left: floral trousers, $50, Topshop; military jacket, $46, Target; fanny pack, $50, Topshop ; turtleneck, $229,J.Crew

No matter how far she runs from her identity, Jerri always returns, frosted hair/lips and all. And you can, too, with just a few basics: turtlenecks, colorful makeup, ill-fitting denim, and anything with fringe. So tuck your shirt into your pants, grab a stolen TV, and you’ll be all set to channel the most stylish mess at Flatpoint High, knowing that in fashion, as in life, there are many second chances. ♦