"The First Cut Is The Deepest" is the sixteenth episode of the first season of One Tree Hill and the 16th produced episode of the series. It was broadcast on March 2, 2004. Nathan must decide which parent to live with after the divorce, but Dan decides to force his hand by threatening to reveal Deb's darkest secrets in court unless Nathan chooses him. Meanwhile, Lucas meets a beautiful stranger who starts his head spinning. Grammy Award-winner Sheryl Crow appears as herself and performs in Karen's Café.
It's the day after Brooke and Peyton's argument. It is quite clear that Brooke is determined to stick to her word. She blanks Peyton on her way in and walks away from her. Jake then approaches Peyton and asks what is going on. Peyton tells him only to confuse Jake. Jake tells her about how Jenny won't stop crying but he has a wedding coming up and Peyton is asked to babysit, Peyton happily agrees as it will keep her away from everything. Before going into school, Dan bribes Nathan with a car but pretends it is a thank you for moving in with him. Even though Nathan is aware of his Dad's obvious meaning, he takes the car to school. At highschool, Peyton is telling Haley about what happened and how Brooke won't ever talk to her again just as Nathan pulls over in his new car. He tells Haley he is keeping it as he might aswell get something from the divorce. Haley tells Nathan she has had no luck with getting the tickets for Sheryl Crow's concert.
In the gym, Skills comes in to find Lucas pushing himself to train again and obviously straining his arm in doing so. Skills tells him to lay off the exercise and stop for a while, but Lucas is determined not to give up on his dream. Leaving the gym, he sees Brooke and apologizes for what he has done to her, but Brooke is bitchy back and tells him he is only sorry because he got caught. Whitey then later finds Lucas to tell him he is needed on the team and when he is ready, so will his position. As Lucas leaves practice, Dan walks in expecting a thank you and be deemed a hero by Lucas, but Lucas does quite the opposite and still sees him as a villain as one thing does not change a person. As he leaves, Dan compliments Nathan's play to grind on Lucas aswell as sarcastically telling Lucas it was a big plan to pull him out the car so he could make his life hell. Nathan tells Dan that he didn't have a choice with who to live with as it is his only way to help protect his mom while Peyton and Brooke continue to argue even when Peyton apologizes, Brooke still won't accept.
Keith has put his garage up for sale and Dan pays him a visit to offer him a business proposition. The deal is that he buys the dealership and would be a silent partner with Keith. Keith immediatley refuses, but Dan doesn't give up. He says that Keith would pretty much have the same job and when he earns back enough money, he can buy the garage back. He says he has turned a new leaf and Keith believes him and accepts his business offer. Nathan meets with Deb only to end in arguing as a stroppy Lucas storms out of a dinner with Haley and Karen due to all the stress he has been having with the game and his love life, not before saying that he is going to change who he is.
Lucas goes to the bar that him and Brooke once went to and uses his fake I.D. to get a drink. As he gives the money to the barman, he is told that a woman has already paid for it. As Lucas looks down the bar, he sees a woman smiling at him, he goes to see her and they start flirting with each other. Lucas begins to get drunk with the woman who introduces herself as Nicki. She leaves the bar and expects Lucas to follow her. Meanwhile, Peyton is in her room drawing Brooke, herself and Lucas shooting at a heart in flames with Lucas' number 3 in the middle of it. As the phone rings, she switches off her webcam and finds it is Karen searching for Lucas. She tells her she has no idea where he could be and Karen asks if she might be with Brooke, but they can't get through to her. With Lucas in mind, Peyton takes a brave step and goes to see Brooke. She tells her that Karen needs her help in finding Lucas. Not caring, Brooke says she won't help but just as Peyton is about to leave, she changes her mind and says she might know where he is.
Looking for Lucas, Karen goes to Keith's garage and finds out is for sale. She offers to pay him back, but Keith still refuses and tells her that he has already sorted it out, not telling her about signing a deal with Dan. Peyton and Brooke arrive at the bar which Brooke thinks Lucas might be at. The bar man tells them about how Lucas left with a woman and Brooke isn't surprised at all, whereas Peyton is, they both decide to stay for a drink even though Brooke does not want to be in Peyton's company. Meanwhile, Nicki and Lucas arrive at a carousel which Nicki used to work at. A hesitant Lucas is dragged in and they begin further flirting before undressing and kissing each other. After being on the carousel, the two of them return to a closed diner where they find something to eat. Nicki says Lucas views life as black and white whereas alot of things are grey. Lucas then asks to know Nicki's darkest secret and instead changes the subject to make him go and find something in the back of the store. As he returns with what Nicki asked for, he finds her gone. Back at the bar, Brooke is looking at the different guys at the bar and feeling nothing for them, instead she would rather hit them, but she is thinking worse about Peyton. Brooke tells her that she can't believe what she did but as for Lucas, he is a guy so she expected it, but not from her best friend. Peyton has to leave for Jake while Brooke doesn't know if the two friends will ever get past what she has done to her.
Arriving home, Lucas apologizes for being out late and a furious Karen calms down and they make up. As Lucas owned up to his mistakes, he realizes what he needs to start doing and Karen is proud of him realizing this. Keith visits Dan at his house and signs the contract to the deal, leaving Dan in charge of the garage. Karen offers Deb a partnership, but Deb resisits as Dan can use it as an excuse in court. Skills goes to see Lucas, he gives him an old basketball which they signed in 4th grade and tells him that no matter what, he always has his friends at the river court. Peyton arrives at Jake's to baby sit Jenny and a nervous Jake gives her a list of numbers incase she needs to contact, Peyton tells him to go and not to worry. As left with the Jenny, she starts crying and Peyton can't find a way to comfort her as when she gives her keys to play with, she puts them in her mouth.
Lucas goes to see Whitey. He tells him that he wants to quit, but Whitey won't let him leave that easily. He says that Lucas will always have that place on the team but Lucas insists that if he needs to, he will understand if Whitey replaces him on the team. Deb goes to see Nathan to tell him the secret Dan is holding against her. She reveals that she met another man and left both Dan and Nathan to live with him during a summer camp when he was younger. Nathan is angry at her and says that she pretty much gave him to Dan because she left him alone. Nathan is so furious he tells Haley he doesn't even want to be a part of the family anymore. Keith returns to his garage and finds that a major change is going on. Unsuprisingly, he finds Dan has not lived up to his word. A new boss is introduced to Keith and a new name is given to the garage, and after trying to leave, Dan reveals he has no way out as he signed a contract.
Back at Jake's house, Jake gets home to see Peyton has made a mobile for Jenny and has calmed her down. Delighted, Jake asks Peyton to stay to watch a movie and Peyton happily agrees. Nathan reveals he is going to petition for emancipation while Brooke and Lucas have another run in. She tells him that all the time they were together she felt inferior to him but by doing this she was stupid. Brooke tells Lucas she doesn't even want to be his friend and brands him as a liar and a cheat. Meanwhile, Sheryl Crow arrives at the closed cafe for a coffee. A star studded Haley makes a deal with her, a song per cup of coffee and Sheryl happily agrees. Nathan and Haley sit down to listen to her perform and one of Haley's dreams is reached. Deb goes to find Dan and tells him about Nathan's emancipation, leaving them both shocked and indecisive as to what to do next. As Jake is cleaning up his house after Peyton left, the door goes and Jake answers to find Nicki there. She asks how her daughter is as a shocked Jake stares at her.
- "Boy meets girl, girl doesn't know what she wants, boy starts to date girl's best friend, girl ruins everything"
- "Oh I saw Dan, he told me that the reason he pulled me from the wreckage was so that he could watch me suffer"
- "He's tall, blondish, kind of a loner"
- "Cheats on girlfriends with skinny blonde bitches"
- "You're never more alive than the moment before you die"
- - Nicki
- "You know, I look around at all these great looking guys and all I wanna do is smash their pretty little faces. Don't even ask what I'm thinking when I look at you"
- "Don't you see what you did? You gave me to him Mom, you knew exactly how he was and you made me Dad's property"
- "Yeah well technically, you can kiss my ass"
- "Do you know, the entire time we were dating, I actually felt inferior to you, what a joke. You are just like every other guy on the planet. You are a liar and a cheater"
- "He's leaving us Dan, and I don't blame him"
- "Big Ballin' (Above The Rain)" - Bigg Blue
- "Never Like This" - Buva
- "There Goes The Neighbourhood" - Sheryl Crow
- "Parking" - The Fuzz
- "Home" - Sheryl Crow
- "Tiny Little Fractures" - Snow Patrol
- "Bleed" - Stone Dogs
- "Lucky Kid" - Sheryl Crow
- "Tell Your Story Walking" - Deb Talan
- "He'll Be Around" - Boss Martinas
- "Don't Forget" - Kid Gloves
- "Breaking Away" - Bosshouse
- "Nothing" - Smashtrax
- "It's Only Love" - Sheryl Crow
- "The First Cut Is The Deepest" - Sheryl Crow
This episode's title originated from the song The First Cut Is The Deepest, originally sung by Sheryl Crow.
- Sheryl Crow is the second musical guest star on the series. Unlike Gavin DeGraw in "You Gotta Go There To Come Back" her music is used throughout the episode in addition to her final performance (with a total of five songs played throughout the episode).
- Sheryl Crow performs the song the episode is named after at the cafe.
- Lucas, Nicki and, later Peyton and Brooke, visit the bar which Brooke and Lucas went for their first date. ("With Arms Outstretched")