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• Actor Allusion: Blair referring to Georgina, played by Michelle Trachtenberg, as a vampire.
  • Chuck, played by Londoner Ed Westwick, gets his haircuts at Piccadilly.
  • Blair compares Chuck to House. Leighton Meester guest-starred on House, playing a teenager with a huge crush on the title character. Coincidentally, Chuck and House are both dark, twisted Jerk with a Heart of Gold type characters, and Ed Westwick and Hugh Laurie are both Englishmen while their characters are American.
    • What makes it funnier is the scene where Chuck is talking to Blair about her British boyfriend and says: "You can't tell me Bertie Wooster is satisfying your needs."
  • Blair mentions herself and Chuck role-playing Wuthering Heights. Ed Westwick had been cast to play Heathcliff in a new remake but was dropped not long before the episode where Blair makes the mentioning aired.
  • A Season Four episode is titled "The Townie" referencing the movie The Town in which Blake Lively has a role. This was the first time they would do this, but not the last (the same season also saw "Panic Roommate" mash up Panic Room and The Roommate (Leighton Meester plays the title role in the latter), and "Easy J" riff on Easy A, in which Penn Badgley appears).
  • In Season 1, when Jenny is trying on dresses at Blair's house, Blair tells her a dress is too Hannah Montana. Taylor Momsen was one of many actresses considered for the role.
  • During the build up to and actual Blair's wedding, Wallace Shawn makes at least two Princess Bride references by name.
• Dawson Casting: All main "teen" cast, with the exception of Jenny (Taylor Momsen is an actual teenager) apply into this trope. Particularly notorious is Nicole Fiscella (Who plays Isabel Coates, one of the mean girls), who is actually almost 30.
• Dyeing for Your Art: Leighton Meester dyed her blond hair brown before her audition, and has to keep it brown whenever the show is filming.
  • The awful dreads they put on Jessica Szohr have to count.
  • Also the ridiculous rat nest that is Taylor Momsen's hair, provided she didn't do it for herself.
• Enforced Method Acting: Billy Baldwin refused to meet Blake Lively before their first scene together because he wanted the experience of seeing your father/daughter again after 14 years to be as real for both of them as possible. He also stated that he pretended Blake was his real life daughter.
• Fake American: Chuck Bass is played by English Ed Westwick.
• Fake Brit: Lord Marcus, played by American Patrick Heusinger. Making it an American playing a Brit who fakes being American. Add to that the scene where Chuck (played by a Brit, as noted above) imitates Marcus' accent to pull a Bed Trick on Blair. A Brit playing an American faking a British accent as done by an American.
• Hey, It's That Guy!: Cyrus Rose is Vizzini. Judging by the way he out-schemed Blair, he's gotten a little better at his planning.
  • Inconceivable!
  • Before portraying Bree Buckley in Season 3, Joanna Garcia played Megan Smith, Sam, and Cheyenne.
  • Before playing Rufus, Matthew Settle portrayed one of the most badass people ever, Lt. Captain Ron Spiers.
    • His daughter is Cindy Lou Who.
  • Lily Humphrey was Femme Fatale Dixie Cousins on The Adventures of Brisco County Junior and Intrepid Reporter Caitlin Byrne on Kindred: The Embraced.
  • One for the UK fans: Mr Smith, the guy Agnes and Jenny visit in Bonfire of the Vanity and who Jenny later returns to for help in launching her fashion line, is the guy from the Orange adverts.
  • Georgina is Dawn Summers, who, for Buffy fans at least, will look 15 for all eternity.
  • In her blond days, Blair stalked House.
    • Even better (and brunetter), she "had a long and storied reign as the gossip queen of Neptune High."
  • Chuck's life was saved in Prague by Fleur Delacour!
    • And Lord Voldemort is Chuck's valet.
  • Juliet was the little devil on Sam Winchester's shoulder.
  • Russell Thorpe was anal-retentive CFO Stanley Babson on HBO's Arli$$, and Doctor Cox's best friend from college on Scrubs.
  • Serena was conned by one of the Winklevii.
  • What about Lizzie McGuire as Vanessa's roommate?
  • The "Valley Girls" Backdoor Pilot features MegPryor as well Dick Casablanca and Gia Goodman with Dan Patch as the antagonist
  • Jenny's model friend and later enemy is Kaitlin Cooper
• Hey, It's That Voice!: Kristen Bell is Gossip Girl, though she's uncredited.
  • Also the Japanese version has Ulquiorra with Hitsugaya as siblings, Marida as Serena and Starkiller as Chuck Bass and Litchi spilling the gossip.
• McLeaned: Bart Bass.
• Mean Character, Nice Actor: Leighton Meester is by all accounts a lot easier to take than Blair Waldorf (which admittedly wouldn't be hard).
  • Georgina is a Rich Bitch Magnificent Bitch bar none. Michelle Trachtenberg is a completely Adorkable Nice Girl.
• Name's the Same: Nate Archibald is also the name of a former NBA player (Wikipedia searches redirect to the player).
• Real Life Relative: Jessica Szohr (Vanessa) and Ed Westwick (Chuck) were dating as well (though, in a bit of a twist, Westwick discovered that Szohr was seeing other men), even their fictional counterparts don't get along very well.
  • Leighton Meester (Blair) and Sebastian Stan (Carter) (broken up).
  • Blake Lively (Serena) and Penn Badgley (Dan) (broken up).
• The Red Stapler: Chuck's trademark scarf sold out within days of the pilot episode airing.
• Romance on the Set: Blake Lively (Serena) and Penn Badgley (Dan) have been dating for 2.5 years. Ed Westwick (Chuck) and Jessica Szohr (Vanessa) dated for 1.5 years, but have supposedly broken up since. Leighton Meester (Blair) and Sebastian Stan (Carter) have dated on and off throughout the show's run, but are supposedly off now.
• Screwed by the Network: The Valley Girls spinoff was picked up, but then cancelled before it could even air.
• Stillborn Franchise: 2008 saw the release of OMFGG – Original Music Featured on Gossip Girl No. 1. There would not be a No. 2 (the CD didn't even include the show's opening/closing music for some reason).
• Throw It In: This ad-libbed dialogue in the last scene from Season Two:

Blair: (after Chuck told her he loves her) But, can you say it twice? No I'm serious, say it twice. Chuck: I love you. I love you. That's three. Here's four - I love you.

• Word of God: Josh Schwartz and Stephanie Savage have cruelly crushed hopes for Vanessa/Rufus, saying that fans who want them are barking up the wrong tree.