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What do crossdressing boy sex videoJack Kerouac, RuPaul, Macy Gray, and Officer Krupke from West Side Storyhave in common? They're all referenced in the Gilmore Girlspilot, of course.

On Oct. 5, 2000, Gilmore Girlsdebuted on The WB and caffeine-fueled single mom Lorelai Gilmore (Lauren Graham) came into our lives for the very first time. As "There She Goes" by The La's played onscreen, Lorelai strolled down an idyllic Connecticut street in the fictional town of Stars Hollow and entered a diner called Luke's. There, she and her 15-year-old daughter Rory (Alexis Bledel) proceeded to make all four references listed above before the show's theme song even began. It was the first of many truly impressive verbal feats on the show, but it was also the start of a riveting pop culture masterclass.

In honor of the Gilmore Girls20th anniversary, we're reflecting on one of the dramedy's most charming trademarks: a deep, unwavering obsession with pop culture.

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Over the course of its seven seasons (and the four-part 2016 Netflix revival) Gilmore Girlsmade hundreds of references to movies, television shows, books, music, celebrities, and noteworthy moments in history. The world has changed a lot over the past two decades, and more than a few aspects of Gilmore Girlshave become painfully outdated. But 20 years later, the show's pop culture references remain evergreen, and will continue to school new generations of fans for years to come.

Watching and learning from Gilmore Girls

As someone who grew up watching Gilmore Girlson the air from 2000 to 2007, I had the unique experience of seeing the show through the eyes of an elementary, middle, and high schooler. The overabundance of pop culture references fascinated me, but because I started watching at such a young age, many of them were also confusing as hell.

I knew that understanding each and every witty reference was key to fully grasping the show's brilliance.

When I first saw the pilot, for instance, my ears perked up when mainstream, accessible references like Oprah, Eminem, and Britney Spears were casually brought up in dialogue. But I didn't have the faintest idea who Jack Keroauc was, the Rosemary's Babyreference went right over my head, and my brain barely registered RuPaul and Flo-Jo as names.

The more I grew to love Lorelai, Rory, and the gang, however, the more I wanted to be in on all of their jokes. I knew that understanding each and every witty reference was key to fully grasping the show's brilliance, so I wholeheartedly committed to pop culture professor Amy Sherman-Palladino's teachings.

The "Gilmore-isms" study guides

Every masterclass requires some quality study material, and Gilmore Girlshas given rise to an array of pop culture bibles over the years. Fans have compiled show-inspired reading lists, movie checklists, and Spotify playliststo help educate themselves and their peers. But in the days of streaming Gilmore Girls on Netflix, the greatest study guides of all can be found in a rather unexpected place: the old-school DVD box sets.

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As hardcore fans who still cherish their favorite television series on DVD can attest, disc six of the Season 1 box set includes a "Bonus Material" section with a special feature titled "Gilmore-isms: Many of the show's witty and memorable wordplays." The two-minute compilation video highlights some of the season's greatest pop culture references, including Richard Simmons, Bob Barker, Emily Post, and Judy Blume.

The montage served as Sherman-Palladino's initial ode to the many references in her scripts. But after the show's second season, Sherman-Palladino reallybegan to embrace the unique pop culture authority that she and her show had over viewers.

The Season 2 Gilmore Girlsbox set includes a physical 18-page "Guide to Gilmore-isms" pamphlet. The DVD insert, which resembles a composition notebook, acts as a Gilmore dictionary and gives "the 411" on the season's most memorable references. In addition to defining dozens of the season's pop culture mentions in alphabetical order — starting with Ad Fab and ending with Zsa Zsa Gabor — the guide lists each corresponding episode, features endearing pop culture doodles, and even shares additional enlightening commentary from Sherman-Palladino and her husband and creative show partner, Dan Palladino.

The Gilmore guides. Credit: nicole gallucci Oy with the pop culture already! Credit: nicole gallucci

The educational booklets appeared in the show's 2nd, 3rd, and 4th season box sets (and possibly the 5th, but I couldn't find mine). And when Gilmore Girls ended, a mega "Gilmore-isms" guide was compiled to help fans reminisce on more than 1,000 of the show's pop culture references past. The gorgeous 43-page book came with the complete DVD bundle, which includes all seven seasons of the series.

Much like the show itself, these physical guides act as time capsules packed with decades-worth of precious pop culture gems. Though not every single reference from the series is included, the books are a reminder of just how committed the show was to treasuring and preserving influential television shows, movies, and music that came before it.

The gorgeous mega guide to "Gilmore-isms." Credit: nicole gallucci Even Gwyneth Paltrow and Chris Martin's daughter, Apple, got a shoutout. Credit: nicole gallucci

Gilmore Girls leaves behind an enduring pop culture legacy

Growing up I poured over these guides, because I knew they were created to help fans develop a deeper understanding and appreciation of the Gilmore world. It's clear that Sherman-Palladino utilized her own expansive pop culture knowledge when crafting the quirky, eccentric characters of Stars Hollow. And in doing so, she helped educate fans of all ages on everything from classic films like Casablancaand Funny Girland noteworthy literature by Marcel Proust and Edith Wharton to early 2000s flops like Glitterand From Justin to Kelly.

While the majority of the references in Gilmore Girlsstill hold up in 2020, certain nods to public figures Brad Pitt and Jennifer Aniston, or Hillary Clinton and Donald Trump definitely hit different. A few references to men like Woody Allen and Harvey Weinstein, both of whom have been accused of sexual assault, also clearly haven't aged well.

Though not everything about the original episodes work nowadays, when it came time to revive everyone's favorite fast-talking mother-daughter duo in 2016, the Gilmore Girls: A Year in the Lifescripts were packed with a whole new slew of pop culture references. If you've watched any of Sherman-Palladino's other shows, like Bunheadsor The Marvelous Mrs. Maisel, you've likely realized that pop culture references are a resolute part of her writing style. They're in her DNA and will likely remain part of her signature flair for the remainder of her career, but she set the precedent for on-screen pop culture obsessions with Gilmore Girls.

"Gilmore Girls" is indeed a lifestyle. Credit: mashable composite: gilmore girls / netflix

The show and its quick-witted characters encouraged curiosity and a pursuit of pop culture knowledge amongst viewers in a way I have yet to see repeated. Gilmore Girlsis the reason I started listening to Nick Drake, Blondie, and XTC as a teen. It's why I added things like Howl,Swann's Way, and The Fountainheadto my reading list. (And later crossed The Fountainheadoff. Team Jess.) It's why I watched old films such as the 1969 dance marathon drama, They Shoot Horses, Don't They? And it's why I knew who Lenny Bruce was long before I watched The Marvelous Mrs. Maisel.In 2006, I'm not sure the average 13-year-old had any clue who Donna Reed, Paul Anka, Carole King, Christiane Amanpour, Natalie Wood, or Madeleine Albright were. But I did, because Gilmore Girlstaught me.

It's been 20 years since GilmoreGirls premiered, but the show is still educating viewers on pop culture of the past. And years from now, the Gilmores and all who interacted with them will continue introducing new generations of fans to old music, movies, celebrities, and books.