The Saddest Moment From Every Season of One Tree Hill

The Saddest Moment From Every Season of One Tree Hill

Welcome to MsMojo and today we’re counting down our picks for The Saddest Moment From Every Season of One Tree Hill.

For this list, we’ll be looking at the most devastating, heartbreaking moments from this teen drama. If you haven’t already, we’d suggest binging all nine seasons before we spoil anything.

There are many of them, so if we missed your favorite sad moment let us know in the comments.

#9: Lucas’ Car Accident
“Hanging by a Moment”

This is the first car accident of many, many car accidents on this show. While on the way to pick up Karen from the airport after her trip to Italy, Keith and Lucas get into a car crash which almost results in Lucas’ death. He dislocates his shoulder and falls into a coma leaving the gang not knowing if he will wake up. But Lucas isn’t the only one this accident affects. The lives of everyone around him are thrown out of whack. Keith's relationship with Karen is effectively ruined. Brooke and Peyton are both devastated. And Haley is scared she may never get the chance to make up with Lucas after their big fight.

#8: Jake Leaves
“The Tide That Left and Never Came Back”

For some reason, Season Two was the one where everyone leaves. Weirdly, Haley leaving Nathan to go on tour with Chris Keller wasn’t even the saddest departure. No, that would go to Jake leaving Peyton to go after his daughter Jenny. Jake could have easily been Peyton's one true love if he could have just stayed in Tree Hill. They were becoming such a lovely little family until Jake’s ex, Nicki, came back into town to muck up the works. When he had to leave Peyton for good to go find his daughter it felt like the end of a true and pure love. Jake’s speech about how much he loves Peyton will shatter your heart.

#7: The School Tragedy
“With Tired Eyes, Tired Minds, Tired Souls, We Slept”

There are a lot of sad moments in the third season. Peyton’s birth mom, Ellie, dying after a battle with cancer was particularly devastating. But even that moment pales in comparison to this one. The time capsule video was released and Jimmy got relentlessly tormented to the point where he brought a gun to school just to get it all to stop. For the first time, his friends really hear about just how badly he's been hurting. Jimmy’s monologue in the tutoring center, and then again in the hall with Keith will rupture your soul. Peyton nearly dies, Jimmy takes his own life, and Dan causes Keith’s death all in one episode. This is hands down the saddest moment in the whole show.

#6: Haley Gets Hit by a Car
“Some You Give Away”

What is it with the Tree Hill gang and car accidents? There’s at least one car-related incident in almost every season of the show. After Nathan gets mixed up with a loan shark, Daunte, who wants him to throw the state championship, he wins the game anyway, enraging him. Daunte tries to get revenge by running Nathan down, but it’s Haley that gets hit when she pushes Nathan out of the way. And if that weren’t crazy enough, Lucas has a heart attack at the sight of Haley’s motionless body. What should have been the greatest night of their lives instantly turns into one of the scariest with the lives of Lucas, Haley, and her unborn son, Jamie hanging in the balance.

#5: When Brooke Had to Give Angie Back
“What Comes After the Blues?”

Brooke just can't catch a break. When Brooke came back to Tree Hill, all she wanted was to start a family. She tried adopting, but she could only get a sort of trial run with baby Angie. Angie needed to get a special operation so Brooke took care of her while she recovered. And just like Brooke excels at everything she tries, she nails it at being a mom too. We all knew from the beginning that the time would come when Brooke had to give Angie back to her family. But knowing that Angie couldn't stay did not make it any easier when she left.

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4: Quentin’s Funeral
“Get Cape. Wear Cape. Fly.”

Quentin started out as such a jerk, but when Nathan and Haley put a little faith in him, he started to turn things around. He became friends with Jamie, helped Nathan with his comeback, and grew to really respect Haley. He had such profound character development in his short time on the show that you went from hating him to loving him in one season. Watching Q's little brother stand in his place in the lineup with the rest of the Ravens, and Jaimie put the cape he made for Q on his coffin is not just one of the saddest moments of the season, but of the entire show.

#3: Haley’s Mom Dies
“The Last Day of Our Acquaintance”

You'd think that this moment would be less upsetting than some of the other character deaths because we don't really spend that much time with Lydia James. But watching the three James sisters suffer as she died was absolutely gut-wrenching. Lydia was the one who believed in Nathan and Haley when no one else did. Without her, we may never have witnessed the absolute couple goals that is Naley. And in the course of her final episode, you couldn’t help but feel for her and the James family so deeply that you cried with them when she slowly and peacefully passed away.

#2: Brooke & Jamie Get in a Car Accident
“Darkness on the Edge of Town”

This was a really heart-wrenching moment. During a terrible storm, a drunk driver knocks Brooke and Jamie's car into the river. Julian happens to pass by and tries to save them but Brooke is trapped. Watching Brooke beg Julian to leave her and save Jamie first is heartbreaking. She ends up drowning in the car and nearly dies. Thankfully, Julian was able to revive her but that was a truly scary moment when it seemed we might lose Brooke. “One Tree Hill” has had many near-death experiences, and everything always works out just fine. But this time, they actually had us believing for a few minutes there that Brooke might not make it, and it was devastating.

#1: Dan’s Death
“Danny Boy”

Dan was always the true villain of this show. He was selfish, and malicious, and hurt everyone in his orbit. He was even responsible for his brother’s death. Eventually he started forward on his redemption arc, but he still managed to be a major jerk and a creep to those around him. But saving Nathan from his kidnappers was his final step in redemption. In his last moments, he finally admitted how wrong he had been about everything. And though this one moment of sincerity cannot erase everything he did in the past, if you can imagine, somehow we actually felt sad when Dan was gone for good.