Gil being a rock musician is because Sebastian Bach is one, having fronted Skid Row.
In A Year in the Life, Doyle is a Hollywood screenwriter. The actor who played Doyle, Danny Strong, is also a Hollywood screenwriter in real life.
Blooper: In a season 6 episode, Rory tells Logan that she lost her virginity to him, when the one she lost it to was Dean. Of course, it's not impossible that she lied to make him believe he was her first, but she doesn't seem like the type who would.
Alex Borstein got to show off both her harp-playing skills as Drella and her skill at playing silly characters as Miss Celine.
Semi-subverted in season 6 when Rory speaks Spanish with Emily and Richard's maid. While Rory admits that she doesn't speak much Spanish and doesn't speak it well, Spanish is actually Alexis Bledel's first language which she still speaks fluently as an adult. Not many people know that Bledel is actually Latina with Mexican and Argentine ancestry.
Sutton Foster, who starred in Bunheads has a small part in two of the episodes as Violet, the star of the Stars Hollow musical.
Julia Goldani Telles, another Bunheads alum, appears as Sandee of Sandee Says. Bailey De Young also pops up as a member of the Thirty-Something Gang.
Mae Whitman, who played Lauren Graham's daughter in Parenthood, is the girl Lorelai gives a doughnut to while waiting in line with Rory.
The second park ranger who tells Lorelai that he needs to see her hiking permit or leave? Peter Krause, Graham's actual boyfriend and on-screen brother in Parenthood.
The first park ranger that Lorelai meets? Jason Ritter, who played a Love Interest to Graham's character on Parenthood
Emily Bergl and Liza Weil are the best of friends in real life dating back to their camaraderie through the New York acting scene of the late 90s, the complete reverse of Francie and Paris's hostility towards each other.
Kathleen Wilhoite plays Liz, Luke's irresponsible, flighty sister. She has terrible taste in men and questionable parenting skills; she ships her teenager off to Luke when she cannot handle him. This is at least the second time Kathleen Wilhoite has played this role. She spent much of the 1990's playing Dr. Susan Lewis' irresponsible, flighty sister with terrible taste in men and questionable parenting skills on ER.
The Waltons is mentioned a few times in the series, but no one seems to notice how much the outside of the Dragonfly Inn looks like the outside of the Walton house or how much Stars Hollow looks like the Waltons version of Charlottesville. They're the same sets on the Warners backlot, of course. There are also a couple references to The Music Man, and River City was also filmed on the same set as Stars Hollow. This makes one of the Music Man references, in which Olivia compared Stars Hollow to River City, a bit meta.
In A Year In The Life, Lorelai comments how Paul is as forgettable as Marvel movies. Sean Gunn, the actor who plays Kirk, was in Guardians of the Galaxy and had an even more prominent role in the sequel, which are both directed by his brother, James Gunn.
Back to A Year In The Life, Rory tells Jess about a spec script for The Mysteries Of Laura, and asks if that's even a show (it is - and Kerry Butler, who plays Lorelai's therapist, appeared on it).
Channel Hop: A demented example when the series was screened in Britain; the first three seasons aired on Nickelodeon of all places (and were prone to being censored and have episodes dropped), to the point of the fandom discouraging any Brit from getting into the series that way. The Hallmark Channel eventually picked it up and carried seasons four and five, before E4 gave the final two seasons their UK debut (and ultimately screened all seven), the first time they weren't subject to censor scissors across the pond.
Dawson Casting: At the time of filming the pilot, Alexis Bledel (19), Keiko Agena (27), Liza Weil (23) and Jared Padalecki (18) were all extremely convincing as sophomores in high school. Milo Ventimiglia was 24 when he joined the show as 17-year-old Jess.
Heavily in season six, and once Amy was out the door, very apparent in season seven as the show was used basically by the CW in order to trap viewers into sampling the other awful wares of their inaugural season without regards to six seasons of well-established continuity or writing by such luminaries such as Jane Espenson.
The new executive producer who came on had some odd baggage, having been slapped with a restraining order by Heidi Klum (his co-worker when he wrote on Spin City) after he wrote a bizarre and offensive one man play performed in New York about how he'd really, really, really like to sleep with her, after which he was involuntarily committed for a spell by his father. Thankfully he left the Girls alone...physically. Characteristically however...
Dean coming back and having his affair with Rory, pretty much so that the network could remind their audience that Jared Padalecki still was there and ready for Supernatural, coming to the WB Thursdays next fall!
Hal Douglas, the voice of the WB, didn't move over to the CW, thus the show lost their authoritative father figure promo voice, replaced with an unknown voiceover artist who you saw more describing the wacky hi-jinks of the earlier double-shot of Everybody Loves Raymond (tonight at 6:30 on CW67!) than working as the Danny Dark of the fifth network. It also sadly proved that the brain trust at UPN rather than the WB was in charge and didn't know what to do with a successful series.
Nickelback's "Far Away" playing in the season seven promo teasing the infamous 'Wedding in Paris' episode. Nickelback is a band that would never go near Lane or Rory's CD players, and Top 40 music was only mentioned in derision or as a necessary evil in the background of dance scenes during the AS-P era.
The cast photos for season seven playing up Lorelai, Rory, Luke and Logan wearing way too much spray tan at the expense of the rest of the entire cast, which didn't get one picture. Again, UPN thinking (as earlier cast photo shoots involved all of the stars and sane photographers).
The continued employment of David Sutcliffe, who only came back in the later seasons after failing as the lead guy in I'm with Her, an ABC sitcom with Teri Polo which happened to be scheduled against Gilmore Girls and was beaten in the ratings by it a few times.
Inverted in A Year Of The Life as the Palladinos were given virtually free reign by Netflix, and the episodes lacked the direction of the original series, included long, random of tangents (the Stars Hollow musical and Life and Death Brigade), wasted time on guests stars, had several fairly offensive jokes (including fat shaming and the treatment of Emily's maid) and the controversial ending. A lot of fans wondered if having a firmer hand to balance out Amy and Dan would have helped those issues.
In-Universe meddling was performed by Terrance, Paris and Paris' dad to set Paris and Rory up as roommates at Yale.
Fake Nationality: Lane Kim, Rory's Korean best friend, is played by a Japanese-American actress. Lane's mother, Mrs. Kim, is also played by a Japanese-American actress. And away from the Kims, Frenchman Michel is played by French-Canadian actor Yanic Truesdale.
Sutton Foster was a huge fan of the show and naturally, after working with Amy Sherman-Palladino on Bunheads, she jumped at the chance to have a role in the Netflix revival. And after filming a scene with Lauren Graham, she burst into tears.
The hosts of Gilmore Guys, a podcast dedicated to analyzing the show, are seen as patrons at the Dragonfly Inn's dining area.
Jason Mantzoukas, a frequent guest on the above podcast because he was a huge fan of the show, appears as Naomi Shropshire's lawyer breaking the book agreement between her and Rory.
Romance on the Set: Milo Ventimiglia (Jess) and Alexis Bledel (Rory). They met when he was cast as Jess and remained together until separating in 2006. It lends quite a bit of Reality Subtext to Rory and Jess' final scenes together.
TJ's brother is played by Michael DeLuise's real life brother David.
Rory and Jess shared a good lot of on-screen chemistry. This was likely due to their actors dating in real life.
The park ranger who No Sells Lorelai's attempts to let her hike without a permit is Peter Krause, Lauren Graham's real life partner.
Real Song Theme Tune: The show's theme is "Where You Lead," by Carole King, but not the original version. The original was recorded in the 70's and is about following a man; due to the sexist connotations, Carole King soon became uncomfortable performing it live. When Amy Sherman-Palladino approached her about using it as the theme song, King said she would rather re-record it. She contacted the song's original co-writer, who tweaked the lyrics to reflect a mother-daughter relationship, and then re-recorded the song with her own daughter.
Reality Subtext: While it's clear that Amy Sherman-Palladino had planned Rory's Wham Line from the beginning, it's a freaky coincidence that Alexis Bledel actually welcomed her first child shortly before filming the revival.
Mia, the owner of the Independence Inn and Lorelai and Rory's surrogate mother/grandmother was played by a different actress in season 7.
Cesar, one of the servers at Luke's Diner was played by a thin, tall Latino actor in the first two seasons, but was only really ever in the background and never had any lines. In the later seasons, Cesar was played by Aris Alvarado, who was chubby and didn't really look anything like the first, but he became one of the town's quirky characters and had the rare scene every once in a while. Viewers could be forgiven for not noticing the change.
Screwed by the Network: Might as well be renamed Screwed by Dawn Ostroff. The WB let Amy do whatever she wanted for six seasons, but once somehow Dawn became the leader of the new CW instead of any one of the WB's competent executives, the show started its stunning death spiral towards the last half of the sixth season, and her meddling with the show to use it as part of a Bait-and-Switch strategy to make viewers forget completely about the well-loved WB and forget UPN ever existed alienated most of the fanbase outside of the Rory/Logan shippers. And even that small win was destroyed with the abrupt series finale where they were broken up. Both Liza Weil and Kelly Bishop (who both rarely speak ill of anyone or anything in their careers) expressed disgust publicly that a proper series finale wasn't filmed as a Plan B in case of cancellation.
Shrug of God: Amy Sherman-Palladino has said that Rory's not above considering an abortion when weighing her life choices together but could also choose to keep it.
Sookie was played by Alex Borstein in the unaired pilot, but she couldn't dedicate her time to the series proper because of her commitments to MADtv. And if she had taken the part, since Jackson was played by her real-life then-husband, it would have been a case of Real-Life Relative as well.
Jess was supposed to appear in the final season, but Milo Ventimiglia refused when Amy wasn't the showrunner anymore. The character was also intended to stay on the show much longer as the Palladinos offered Milo a six-year contract, but he declined in favor of a two-year contract and the option to drop in any time he was available, resulting in Jess's Commuting on a Bus.
Sookie was originally going to be a lesbian, but at the time the network executives didn't like the idea.
Liza Weil had actually auditioned as Rory, but Alexis Bledel won the role because of her strong resemblance to Lauren Graham. However, Amy Sherman-Palladino saw potential in Weil and wrote Paris Geller especially for her to perform.
Jess almost got his own spin-off show, to which the season 3 episode "Here comes the son" would have been the pilot to. However, it turned out that filming at Venice Beach where it would have been located would have been too expensive, and so it was cancelled.
Had Amy lasted until the end of the show, Rory's pregnancy from the revival would still have happened, but she would have found out she was pregnant at 22 - instead of 32 - just as she graduating Yale and about to do her Masters.
Written-In Absence: The show couldn't get Madchen Amick to reprise her character in later years, so the 'Sherry running away to Paris' plot was created to conveniently allow her to be absent without writing out the character.
Sherilyn Fenn played Jess' stepmother in the Poorly Disguised Pilot, and later played Anna Nardini, the mother of Luke's lovechild.
Marion Ross played Richard's mother and shortly after, Richard's cousin Marilyn after Trix passes away.
Alex Borstein originally portrayed Drella, the harpist at the Independence Inn in season 1. A few seasons later, she played Miss Celine, Emily's fashion consultant in a few episodes. Alex Borstein was originally going to be Sookie, but couldn't because of contract obligations to MADtv. A short clip can be found in the special features of the season 1 DVD.
Kirk showed up as Mick in an early episode to install an alarm. Fanon claims that he didn't bother to change the name tag and ran with it.
Rose Abdoo, who plays Gypsy, also plays Emily's new maid Berta in A Year in the Life.
Emily Gilmore's jewelry is actually Kelly Bishop's own jewelry as she is allergic to the nickel plating used on costume jewelry.
According to one of the costume designers, part of the reason the show's wardrobe avoided looking dated was because Amy Sherman-Palladino mandated that no midriffs be shown. She disliked how the fashion of the decade was mostly midriff-baring, and because of the show's setting in Connecticut during fall and winter, she figured it would have been too cold for that kind of clothing anyway.
According to Milo Ventimiglia, he really did read all the books Jess was shown reading in the show but even he couldn't finish The Fountainhead.