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A ‘One Tree Hill' Superfan’s Ranking of the Top 10 Most WTF Moments of the Series

When One Tree Hill premiered 20 years ago, back in Sept. 23, 2003 (if you can believe!), I was just a young tot who was glued to my television set, drooling over Chad Michael Murray. I recently did a full rewatch and honestly could not believe my C.M.M. passion, considering how hot Nathan is and how much he fought for his love for Haley. But I digress… we all make mistakes when we’re young.

Not only did I do a full rewatch this year, but I also visited the town where all of the OTH action took place: Wilmington, North Carolina. So yeah, I guess you can call me a superfan. I visited the actual Naley bench, where Nathan gave Haley that Cracker Jack bracelet and said, “Don’t say I never gave you anything.” I checked out the Tric club IRL and acted out my own scenes in the room that was recreated to look like Peyton’s bedroom where Brooke screamed, “He’s on the damn door, Peyton!” And, last but certainly not least. I visited the iconic OTH opener bridge where my man C.M.M. ominously and broodingly dribbled a basketball with his hood up like the iconic Sad Boi he is. 

All this to say, in honor of the 20th anniversary of the One Tree Hill premiere date, I decided to write up and reflect on the most WTF moments from the series because let me tell you, there are a lot of them. 

From dogs eating beating hearts to almost hooking up with your wife’s sister, these are my top 10 WTF OTH moments, ranked from 10 being the least WTF to 1 being the most WTF.

  1. Brooke Has a Multi-Million Dollar Business at 22 Years Old

Okay, we get it, her mom Victoria (who was seemingly just a housewife until she became a fashion mogul with Brooke?) did help her, but still. In season five of OTH the cast is aged four years and we catch up with them post-college. Somehow Brooke got her degree and a multi-million dollar fashion empire in that short amount of time? And she’s famous enough to be hounded by paparazzi? It’s the OTH universe, baby, and we’re just living in it.

  1. Nathan Almost Hooks Up With Hailey’s Sister

In season 2 we meet Haley’s older sister Taylor, right when Haley and Nathan are having marriage trouble. Do you smell the drama? When I did my rewatch, I remembered how much this episode haunted me as a youth and how much it still haunts me to this day. I cannot envision a world in which a sister hooks up with her sister’s man. That’s just like, beyond the girl code and would never happen. They have us thinking Nathan and Taylor are going to hook up for the whole episode until it’s revealed that… they didn’t. But there was a lot of flirting and even physical lower back touch, so yeah, it disturbed me.

  1. Rachel Gatina Marries Dan Scott

Season 7 (the first season without Peyton and Lucas!) starts out with a bang when it’s revealed that Rachel Gatina marries legend and villain Dan Scott. This is pretty WTF, considering Rachel is Nathan and Lucas’ (Dan’s sons) age and that Dan met Rachel while she was… um… sleeping with him for money. But you know, nothing’s truly out of character for these two OTH favorites.

  1. We’re Supposed to Find Millie Not Hot, A Total Nerd

Millie is Brooke’s fashion/personal assistant and we’re introduced to her character in season 5. Millie is geeky because she wears glasses (!!) and nervous all the time even though she’s amazing at her job and is actually one of the most stunning actresses I’ve ever seen on TV. But because she wears glasses and falls for Mouth, we’re supposed to think she’s just a total loser who got lucky to be in the fashion industry. I reject this notion!

  1. No One at Tree Hill High Had Any Parents

Obviously Karen of Karen’s Cafe is the most present/iconic parent, but even she leaves for Italy and leaves Lucas to have sex with his girlfriend in his mother’s house, have a pregnancy scare, get a tattoo, and almost die in a car accident at the age of 17 years old. 

Nathan somehow gets emancipated from Dan and Deb without any episodes explaining how exactly he managed to do that when both of his parents were financially stable and willing to parent him. Haley’s parents “go on an RV tour across the country” and leave their 17-year-old newlywed daughter alone with her new husband. Peyton’s dad is a fisherman? And is never to be seen again, and Brooke’s parents leave her alone with a big empty mansion and a credit card and her mother Victoria isn’t seen until season 5. No wonder these kids got into so much drama.

  1. Psycho Nanny Carrie

This is truly an iconic saga in the series and takes place when we flash-forward four years after the crew graduates high school. Nathan and Haley’s son is now 4 and he needs a nanny! It’s too bad that this nanny is obsessed with him, kidnaps him, and then later kidnaps Dan Scott in her weird at-home hospital bunker room, all in an effort to “be a mother.” Honestly, kudos to the writers because I was on the edge of my seat for this whole multi-episode plotline.

  1. Pete Wentz Dates Peyton

Yes, Pete Wentz of Fall Out Boy, which, if you’re currently a teen, was an alt rock boy band from the early 2000s that dominated the alt scene. This might not sound so insane, except when you consider the following: Why was a touring band member so willing to chill in random North Carolina for so long? And the fact that Pete Wentz was an actual man and Peyton was a 16-year-old high school student (gag).

  1. Dan’s Heart Gets Eaten by a Dog

It was hard to write that sentence without cracking up. Our glorified villain Dan Scott needs a heart transplant, but no one in Tree Hill believes he deserves one because he shot and killed his beloved brother Keith Scott. That’s why a dog who was casually passing through in a hospital (isn’t this a health code violation?) gobbled up the heart when no one was looking. Iconic!

  1. Peyton’s Stalker Brother Derek

I want to start out this section by saying the actor who played Derek (Matt Barr) is one of the hottest people I’ve ever seen, and I threw Chad Michael Murray out the love window when Derek came onto the scene. Sure, Derek was a teen boy with violent and stalker tendencies who pretended to be Peyton’s long lost half brother and subsequently kidnapped her multiple times. But that smile! I actually saw Matt Barr at a spa in Montreal once and went up to him and told him how much I loved the show. He was so nice and still as beautiful as ever. Call me! 

  1. The Fact that Teenage Boys Could Express Their Emotions in Full Sentences

This takes the cake for the most WTF moment because, again, I watched OTH for the first time when I was in grade school, and I was fully expecting to enter high school and have all of the hottest boys not only fall in love with me, but profess that love in complete, full sentences. I have to say, 20 years later, I still don’t think guys my age can manage this. So I’ll never forgive OTH for setting me up for this failure all those years ago. This simply does not happen in IRL and it’s absolutely the most shocking part of the entire series. 

Brittany Leitner
Brittany Leitner
Brittany Leitner is a freelance journalist and poet based in New York City and originally from San Antonio, Texas. She previously held editorial roles at Elite Daily and The Dr. Oz Show. Her work in digital journalism earned her a Digital Health Award in 2019, and her writing has been published in Bustle, Cosmopolitan, Oprah Daily, Shape, and more. Her poetry has appeared or is forthcoming in Palette Poetry, Gasher, Cutthroat, and New York Quarterly. Follow her on Instagram @britariail.