15 moments in 'Gossip Girl' that were intended to be serious but turned out to be comedic gold

jenny standing next to a fire on gossip girl georgina holding a baby on gossip girl
"Gossip Girl" was a drama, but there were some laughably over-the-top moments.The CW
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  • The CW's "Gossip Girl" was full of dramatic moments, but some of them ended up being pretty funny.

  • It's hard to take Blair seriously when she does a striptease with her iconic headband accessory.

  • Serena and Vanessa's "Guitar Hero" battle was also bizarre to watch.

Serena throws her phone away after a "Gossip Girl" blast.

serena tossing her flip phone in the trash on an episode of gossip girl
Instead of ignoring the blast, she threw her whole phone away.The CW

Early on the first season, Gossip Girl posts that Serena has lost all her friends and her potential boyfriends.

Serena sees the blast while going through old photos of her, Blair, and Nate on her phone.

But what may have been a moment to sympathize with Serena's newfound loneliness became laughable. Instead of just deleting the photos, Serena threw her phone into the trash.

Blair removes her headband during a striptease.

blair taking off a headband on an episode of gossip girl
Blair was known for her iconic hair accessory on the show.The CW

The start of Blair's season-one downward spiral began with her performing a striptease at Chuck's club opening.

Gossip Girl's narration during the scene, as well as Chuck's reaction, make it clear that this worrying moment is out of character for Blair.

But watching Blair try to sensually remove her headband just makes the entire scene comedic.

Vanessa and Serena fight for Dan's attention with a "Guitar Hero" battle.

serena playing guitar hero on an episode of gossip girl
Serena gives a dramatic performance of "Free Bird" while playing "Guitar Hero."The CW

When Serena and Dan start dating, Vanessa is uncomfortable with their relationship and jealous of Serena.

The two girls hang out for the first time when Dan brings Vanessa to Blair's birthday party, and Vanessa and Serena end up in a "Guitar Hero" battle.

After a lengthy sequence of party guests enthusiastically cheering Serena on while she plays "Free Bird," Vanessa steps up to challenge her back with "Cherry Pie." But before she starts, she spills a secret Dan was keeping from Serena about his mother.

Serena and Dan get into a fight over this, but it's hard to care about the tension immediately after watching Serena perform dramatic hair flips while pretending to play the guitar.

Nate gets into a fistfight during a cotillion and continues fighting in the background when Blair walks away.

nate grabbing carter by the jacket during an episode of gossip girl
Chuck manipulated Nate into fighting at the debutante ball.The CW

On season one, Serena and Blair are presented as debutantes at the annual cotillion.

Near the end of an episode full of drama, Chuck eggs Nate on and makes him think Carter Baizen has a thing with Blair. After sufficient prodding, Nate punches Carter in the middle of a dance.

Blair's dress is ripped when they start fighting, so she quickly walks away with Serena. But Carter and Nate can still be seen flailing on the ground in the background during the ridiculously long fight scene.

Blair sabotages a girl's chances of getting into college with a Flo Rida song.

nelly sitting on the floor studying on an episode of gossip girl
Nelly is also trying to get into Yale.The CW

Blair decides that her biggest hurdle to getting into Yale is beating Nelly's SAT score.

To sabotage Nelly, Blair plays a Flo Rida song after hearing that Nelly's boyfriend broke up with her at a Flo Rida concert.

Blair then sets up a conversation between Nelly and her ex that causes the girl to get no sleep and spend the night before the SATs sobbing.

The situation is extremely cruel to Nelly, but knowing that a single Flo Rida song is her undoing is hard not to laugh at.

Jenny just watches Agnes light her designs on fire.

jenny standing next to a burning trash can on an episode of gossip girl
Jenny and Agnes were designing a fashion line together.The CW

On season two, Jenny moves in with Agnes after fighting with her dad, and the two start designing a fashion line together.

But when Jenny decides to do it on her own, Agnes kicks her out, grabs all of Jenny's designs, and sets them on fire.

Jenny and Agnes are still arguing before Agnes lights the match. But instead of physically trying to stop her, Jenny just watches her work go up in flames while yelling, "What did you do?"

But it's hard to take the whole scene seriously with dialogue like Jenny screaming, "Are you insane?" and Agnes responding, "Yes, I'm insane, Jenny."

Dan reveals he has a secret sibling in a Dylan's Candy Bar.

vanessa and dan standing in a dylan's candy bar on an episode of gossip girl
Dylan's Candy Bar is a chain that started in New York.The CW

After Dan finds out his father and Serena's mother had a child together, he confesses the news to Vanessa while they're at Dylan's Candy Bar.

His decision to reveal this huge secret in the middle of a crowded candy store is already odd. And the entire scene feels more like an ad for Dylan's Candy Bar, with serious dialogue about the secret sibling added in.

The store's logo is visible in every shot of the scene, and Vanessa keeps mentioning the candy they have available by name as she talks about how amazing the selection is.

The school play is ruined when everyone decides to air out secrets onstage.

characters on stage performing a school play on gossip girl
There's a plot around a school play on season two.The CW

Tensions are high during the school production of "Age of Innocence" on season two.

Nate is jealous of Vanessa's interactions with the director, Julian, and Blair is trying to figure out who sent Gossip Girl a tip about her.

Nate ends up breaking character and ranting about Julian and his family's financial problems, which prompts everyone else on stage to air out their grievances with each other as well.

The moment is theoretically humiliating for everyone involved, but it's fun to watch as the usual drama unfolds with the main characters in period costumes.

Lily's past is revealed in 80s flashbacks that include an outfit montage.

brittany snow as young lily in a flashback on gossip girl
Brittany Snow played the younger version of Lily on "Gossip Girl."The CW

Serena's mother, Lily, has a complicated past that includes multiple husbands and a serious relationship with Dan's father, Rufus.

During the second to last episode of season two, viewers find out more about Lily through flashbacks of her time in California in the 1980s.

The episode occurs during a rough period of her relationship with Serena in the present day and is intended to show how similar she and her daughter are.

But it's hard to take it seriously. The flashbacks have a noticeable filter over them, feature upbeat outfit montages, and are inexplicably intercut with present-day moments that remind viewers what the show looks like when it isn't trying to launch a failed spinoff attempt.

Every student reads a "Gossip Girl" blast during graduation.

blair and serena looking down at their phones during their high school graduation ceremony
Gossip Girl didn't even let them get through the ceremony.The CW

Not even their own high-school graduation could keep the students from reading a Gossip Girl post.

In the middle of the ceremony, Gossip Girl posts to call Nate the "class whore," Dan the "ultimate insider," Chuck a "coward," Blair a "weakling," and Serena "officially irrelevant."

Every student seems utterly shocked, even though they've read far worse blog posts about themselves.

The beeps of phones going off in the middle of graduation — combined with a close-up of Serena's tassel pinned directly to her hair sans cap — make everyone's misery comical. And afterward, the adults in the room act like absolutely nothing happened.

Dan is intimidated about having sex with Olivia after watching her sexy vampire movie.

hand holding endless knights trilogy dvd on an episode of gossip girl
Dan dates actress and fellow NYU student Olivia Burke on season three.The CW

Dan starts dating famous actress Olivia Burke when they're both at NYU on season three.

At the beginning of their relationship, Nate shows him her "Endless Nights" movie trilogy, which includes sex scenes where Olivia pretends to orgasm. After watching, Dan is too intimidated to have sex with her, fearing that he won't live up to her vampire love interest.

The two are able to overcome this, but it's hard not to laugh at the incredibly cheesy fake-movie scene.

Blair doesn't notice that Vanessa is holding a microphone during the freshman toast.

vanessa holding a microphone while talking to blair on an episode of gossip girl
Vanessa and Blair both want to give the freshman toast at NYU.The CW

On season three, Vanessa and Blair compete to give the freshmen toast at NYU.

Before the toast begins, Vanessa tricks Blair into arguing with her. Blair tells Vanessa she thinks she's superior to her and admits to manipulating and lying to Chuck to steal the toast.

But Vanessa reveals that the entire speech was being picked up by the microphone she was holding, and everyone at the event overheard Blair's insults.

Blair's inability to see the microphone that was barely hidden behind an awkwardly placed bag is the least plausible secret recording since the webcam moment in "High School Musical."

Olivia sings a Lady Gaga song while heartbroken over the threesome she had with Dan and Vanessa.

dan and olivia holding hands on an episode of gossip girl
Dan directs a version of "Snow White" with Lady Gaga songs.The CW

Dan decides to create a modern version of "Snow White" that uses Lady Gaga songs on season three — the singer even makes a cameo on the episode.

Olivia walks onstage singing an offkey rendition of "Love Game." But she doesn't make it through the whole song because she's heartbroken after realizing Dan is in love with Vanessa.

She picks up on this during the threesome they had on a previous episode but doesn't show her hurt feelings to Dan until the performance.

It's a bizarre setup for one of the most ridiculous moments on the entire show. Plus, it's even more amusing knowing that Hilary Duff, who plays Olivia, is a far better singer in real life.

A Thanksgiving dinner erupts into multiple fights while "Whatcha Say" plays for several minutes.

serena and tripp sitting at thanksgiving dinner on an episode of gossip girl
"Gossip Girl" is known for its memorable Thanksgiving episodes.The CW

"Gossip Girl" has plenty of memorable Thanksgiving episodes, but season three's stands out for its odd choice of background music.

Before dinner even starts, Jenny confronts Eric over sabotaging her at the cotillion, Serena's affair with a congressman is revealed, and Blair accuses her mother of being pregnant.

While everyone is arguing, Jason Derulo's "Whatcha Say" plays at a bizarrely loud volume for several minutes.

It's difficult to take any of the dinner conflicts seriously when the song is on.

Georgina pretends that she had Dan's baby.

georgina holding a baby on an episode of gossip girl
Georgina is the source of a lot of drama on "Gossip Girl."The CW

Georgina comes back to New York at the beginning of season four with an infant she claims is Dan's son.

Dan and Georgina co-parent for a brief moment before Georgina disappears and leaves Dan to care for the baby himself.

Of course, the baby isn't Dan's at all, and this plotline is completely ignored after just a few episodes.

Dan suddenly believing he's a teen father should be more emotional than funny. But watching Georgina hold a baby and act maternal is so out of character that all their scenes together become comedic.

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