Jenny was one of the stranger characters in Gossip Girl. She didn’t know whether she was coming or going, and as a fourteen-year-old struggling to get attention when surrounded by older, more popular girls, she made a few pretty weird decisions.
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Aside from being the sister of Gossip Girl himself Dan Humphrey and the father of ex-rocker Rufus, there was a lot more to Jenny than you may remember. We’ve collected ten things about the character that aren’t presented on the surface.
10 She Was A Drug Dealer
Considering Gossip Girl lasted six seasons, each filled to the brim with twenty-four episodes, there was bound to be some padding and a few storylines that didn’t exactly feel necessary. One of those was Jenny’s incredibly brief stint as a drug dealer.
The season three episode ‘The Hurt Locket’ shows Jenny meeting Damien and becoming involved in his drug-dealing operation. She eventually repels his advances and ends their connection, but not before Rufus is informed of his daughter’s questionable line of work.
9 She Has A Half Brother
This was one part of the Gossip Girl story that really seemed to be glossed over, especially when you consider how important it feels like it should be. We eventually learn that Rufus and Lily had a son together before Serena, Eric, Jenny or Dan were born, meaning Jenny has a half-brother, and more importantly, Serena and Dan are literally related (they still get married though!).
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For some strange reason, this whole story comes out and gets everyone talking for a few days, then just dissipates into something no one seems to care about or even mentions ever again.
8 She Moved To London
After her exit from the show (which we’ll get to in a moment), we don’t see a lot from Jenny. She is banished from the Upper East Side by Blair, who shouldn’t really have that sort of power but we’ll let it slide, and only appears in season four via Skype.
Season five is the one season in which we never see a glimpse of Jenny, and we only get one small tidbit of information on her whereabouts. Apparently, she graduated high school while living with her mother Alison, then moved to London.
7 Her Colours Darken With Her Personality
Visually, Jenny was always quite the spectacle. Fashion was her thing, so her character was shown to make a particular effort in how she dressed. In fact, Taylor Momsen herself has mentioned how much effort the wardrobe team put into her look.
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Much like the clothing in Breaking Bad, Jenny’s wardrobe darkened along with her personality. In the earlier seasons, she was frequently dressed in yellows and pinks, reflecting her bubbly young personality. As she became more fierce and aggressive, these clothes took a turn towards greys and blacks.
6 The ‘J For Waldorf’ Line
In a blink and you’ll miss it moment at the end of the show, Jenny’s final appearance shows her holding a Waldorf bag. Not only does this wordlessly suggest that she and Blair eventually set aside their differences and made up (which ended Jenny’s ban from the Upper East Side), but also that the two worked together.
In fact, Jenny ended up being a successful fashion designer by the time the series finale came about, even landing her own line called ‘J For Waldorf’ with Waldorf Designs.
5 Jenny In The Books
While the books and series are actually relatively consistent in their portrayal of Jenny, there are a couple of discrepancies. While dating Nate, it is revealed that she is a keen artist. This isn’t a complete difference, but we certainly don’t see her painting portraits of him in the show as we did in the book.
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Furthermore, her look was quite different. The book described her as very short, brown-haired and as having very large breasts thanks to intentionally taking medication with that effect. In the show, well, she looked like Taylor Momsen.
4 Jenny’s Spin-Off
For a very brief period before The Pretty Reckless really took off, it was thought that Jenny was going to head off to front her own spin-off show that followed her adventures at boarding school. Obviously, these rumors were false.
Another Gossip Girl that never came to be was Valley Girls, which was supposed to begin off the back of the flashback episode of the same name, following a young Lily Van Der Woodsen.
3 Taylor Momsen Was In The Grinch
The Grinch Who Stole Christmas is a Christmas classic that came out seven years before season one of Gossip Girl. At the time, Taylor Momsen was just seven years old.
She made her acting debut as Cindy Lou Who in the film, almost unrecognizable in comparison to the version of herself in Gossip Girl and the powerful rock singer of 2020. Her role in the kid’s classic even saw her nominated for a fair few awards.
2 And Then She Left To Be A Rock Star
Everyone knows that Taylor Momsen left Gossip Girl. Banished by Blair and using her fresh start to get going on a fashion line, it was plain sailing for the fictional teen. However, sailing was even plainer for Taylor Momsen herself, who stepped back from the show and straight into the limelight of the music industry.
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She now fronts The Pretty Reckless, a band she formed a full year before leaving the show. Their debut album Light Me Up came around the same time, and since then they have had some impressively big hits and regularly play huge shows and festivals.
1 But She Did Come Back For The Finale
Momsen’s only acting credit post Gossip Girl is also Gossip Girl. She left the show and acting behind permanently in 2011, focusing on The Pretty Reckless exclusively. She has explained that she has no desire to return to acting, and with the success of the band, it seems unlikely that she ever would.
However, her one break from her newfound retirement came in 2012, where the character made a very brief reappearance during the wedding at the very end of the show. Don’t expect to see her in the reboot.
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