Courtney doesn't seem to hate Chris much initially until her first elimination in the series as the votes were tampered with but Chris refused to change it. Determined to get justice served, Courtney promised to sue the show for her unfair elimination, but it is revealed in the special that she failed. When it is discovered that she would not be participating in Total Drama Action, Courtney once again sues the show and finally succeeds with the help of her highly-paid lawyers. Being forced to bring her to the show mid-season, Chris begrudgingly complies to all of Courtney's demands including having proper access to better luxuries, making it seem as if Courtney runs the show, otherwise he would suffer another lawsuit from her again. In addition, Courtney would threaten to call her lawyers again whenever she is not happy. As a result, Chris greatly dislikes Courtney as her actions had drastically decreased his salary. However, there are times it seems that Chris like her due to the drama she caused especially those involving Duncan and Gwen.
After Total Drama Action, their conflict becomes worse, as Courtney sues Total Drama in order to debut onto the show. Chris is not pleased by this, due to Courtney invalidating his authority. Courtney further angers Chris by demanding special treatment, and gets it by abusing her lawyers. Chris, in One Million Bucks, B.C., shows immense hatred toward Courtney due to this aspect, and even goes as far as trying to make the others dislike her. In Total Drama World Tour, their conflict subsides, except for a few times where Chris angers Courtney. In Total Drama All-Stars, Chris initially placed her on the Heroic Hamsters but after seeing her behaviour during the first few episodes, Chris transferred her to the Villainous Vultures, seeing that she is a much better villain than a hero, much to Courtney's displeasure as not only this would make her look bad to public, Gwen is also on the team. Chris would eventually put their friendship to the test but the two of them manage to make amends. Near the end of the season, Chris would once again play a role in Courtney's elimination by changing the rules of the challenge the last minute when she is about to win.
Chris informs Courtney that if she chickens out of the cliff dive, her team will hate her for it. Later, Chris shows concern over Courtney's swollen eye.
When Courtney is declared eliminated, she vehemently refuses to go and demands a recount of the votes, believing there to be something wrong. Nonetheless, Chris and Chef Hatchet roughly grab her by both arms and drag her down the Dock of Shame, then throw her into the Boat of Losers. Angered by her unfair elimination, Courtney threatens Chris and tells him that he "would be hearing from her attorney" beginning their long conflict as well as Courtney's first attempt to sue the show.
When Courtney runs into a wall with a fake forest background painted onto it, she notices a camera at the top of the wall and starts yelling angrily at Chris, as she is sure that he is watching her somehow. Chris and Chef are, in fact, watching the live video feed from the camera at that moment, from the comfort of Playa Des Losers. Chris proceeds to mute Courtney to ignore her and her obnoxious yelling. Later, when Courtney finds out that she would not be competing in Total Drama Action, she is enraged and loudly protests. Chris, however, simply shushes her and reminds her that the fine print prevents her from doing anything different then what he tells her to do.
When Courtney returns, Chris has to read a pre-prepared speech that makes him sound enthusiastic about her return, even though he is not excited about it at all and simply muttered the parts that compliment her. After the Screaming Gaffers win, Chris awards the losing team with Courtney, much to her annoyance. Later, at the elimination ceremony, he informs all the other members of the Killer Grips that they are not allowed to vote for Courtney, since the show couldn't afford anymore lawsuits. He then softly mutters that, as a result of Courtney's lawsuits, his massage budget had been sliced in half. Even so, everyone votes for her but since she is immune, Owen is eliminated instead. When Beth, Lindsay and Justin demand that Owen gives a farewell speech, Chris allows it despite Courtney's protest as there is nothing in her contract stating he couldn't do so.
In addition of bringing her back to the game, Chris begrudgingly reveals to the other contestants that Courtney's lawsuit has forced him to obey all of Courtney's demands including having access to better facilities. At the end of the episode, Chris sends an intern to retrieve the piece of Courtney's hair that Heather cut from her as Chris states that he would receive another lawsuit if he doesn't.
After Courtney told the others about her deal, Chris complements her by saying that is one of the reasons why they picked her because they love her being "nasty." She is seen glaring at Chris when he told her that she and Lindsay are going to the local cheese factory.
When Lindsay claims that Courtney "stepped" on her "Invisible Jet," Chris deducts points from Courtney's original score, upsetting her. After Courtney wins the challenge, she begin to use her "super powers" again, annoying Chris to the point he threaten to change the results if she continue to use it again.
While Courtney is trying on the glass boot, Chris says that Courtney got role as the princess, in fear of the boot breaking on her and the show receiving another lawsuit. Later in the episode, he tries to advertise her dolls, The Princess Courtney doll, as well as the Princess Courtney CD. At the award ceremony, Chris reveals that he is changing the Princess Courtney dolls into Princess Beth dolls as Courtney's lawyers wanted 80% profit from the merchandise, which he would never agree to give them.
Courtney constantly demands a prize from Chris for being the first to guess his riddle, and later be the first to bring in some DNA samples from another contestant. Although Chris initially refuses her requests, he finally gave her a bag of cheese puffs as her "reward" just to get her to shut up, obviously annoyed with her as he did so. Also, when he was "murdered," he set it up so that Courtney looked like the murderer (even though he was still alive).
When Owen returns, Courtney tells Chris that it isn't fair and that she is going to call her lawyers. However, when Chris told her that Owen has sued that show for his broken jaw, making them responsible for his food hallucinations, Courtney glares at him. After Courtney completes the second challenge, she opens the bag of goodies she receives only to find an autobiography of Chris much to her annoyance.
During the talent contest, Courtney feeds Chris and Chef food, however, she actually serves them her animal buddy's lunch. While serving the food, Courtney has a smirk on her face. Throughout the episode, Chris laughs at Courtney for fighting with her animal buddy.
Just as Courtney begins to ask a question for the final two, Chris suddenly cuts her off and states that the show ran out of time for questions, which makes it the time for the eliminated contestants to vote. Courtney starts to protest, but Chris makes a silent slicing motion across his neck at the camera, and an off-screen technician quickly muted Courtney just as she starts to scream.
When Courtney asks Chris why everyone's voice was dubbed, Chris said nobody likes the way they sound and apologizes; Courtney glares at him and said that he's not sorry.
Chris tells Courtney that she has to pull the dogsled for Team Amazon due to her and Heather arriving simultaneously and Chris merely choosing her because her name came first in alphabetical order, in which Courtney complains to him.
When Sierra reveals that Chris was in a boy band, Courtney is one of the contestants that is seen laughing at him in the confessional.
When Chris continues to speak in the loudspeaker, Courtney complains to him, saying that he doesn't need to speak in there. Though, after Courtney says that, Chris continues to speak in the loud speaker.
When Gwen and Duncan sing Greek Mix, Courtney finds that she can't hear the lyrics, so she requests Gwen and Duncan to speak up, but Chris immediately shushes her.
During Blainerific, Courtney sings about her disgust at Chris for letting Blaineley onto the show and there must've been a rule against it. However Chris butts in and sings that rules didn't matter since Blaineley was a "ratings jewel".
After Courtney loses the first challenge, Chris reveals that she would be sitting at the "Losers Bench" to which Courtney protests that she isn't a loser. When it is discovered that Courtney is helping Alejandro to cheat, Chris gives her a lion dancer's mask to prevent her from eating his food. During the elimination ceremony, Chris decides to eliminate both Courtney and Blaineley in order to save budget instead of having another tie-breaker like before. Before she leaves, Courtney threatens to sue the show again but Chris isn't afraid of her this time. After Blaineley tells everyone that she was Total Drama's first choice for host, Chris shoves the two girls out of the plane.
When Chris says that the winner is not decided by a vote, Courtney yells at him, as she states that he said that they would have a major role as the helpers of the final two in the challenge. Later, Courtney is seen laughing at Chris when Ezekiel crash landed through his boat.
Once the contestants make it to the beach, Courtney is mad at Chris for tossing them out of a helicopter and even tells him that he has to pay for her dry cleaning, only for Chris to show her a new set of contracts forbidding him to do so. When Courtney tells Gwen the reasons why she is a villain, Chris agrees with her.
After the Heroic Hamsters won the challenge, Chris announces that Courtney's wasn't very heroic in the challenge, due to her cowardice and using an injured Sam as a human shield. Though Courtney claims it her survival instinct took over, and any other contestant would have done the same. As a result of her actions, Chris deems Courtney no longer fit to be in the Heroic Hamsters and makes her switch teams with her ex-boyfriend, Duncan, to the Villains team. Before the team switch, Chris insist that the Hamsters select Courtney to be exiled on Boney Island but Cameron volunteers instead.
When it is Gwen's turn to spin the Wheel of Misfortune, Chris makes it stop at a slot with Courtney's picture on it. The two girls refuse to fight each other as their relationship has improved ever since Gwen had dumped Duncan. However, Chris shows several video clips of Duncan and Gwen making out in order to provoke Courtney to attack Gwen. After they fight each other and then make up afterwards, Chris gives the girls two points out of kindness, giving the Vultures enough points to achieve victory.
At the end of the challenge, Chris does not allow Courtney to give her gross sundae to Scott and states she won't get anything else to eat until she finishes the gross sundae that Courtney attempts to give to the hungry interns. Chris then states he wouldn't have fed the sundae to his interns after Courtney put chocolate coals on it and a bird vomited on it. Courtney attempts to blame Mike for ruining the chocolate sauce, but Chris says that she was the one who put the coals in the sundae in the first place. Courtney asks if she is supposed to have skipped the chocolate sauce and a frustrated Chris states she could have done so. During her elimination, Courtney tries to convince Chris to keep her in a while longer because she hasn't finished eating her ice cream yet, but Chris sarcastically tells her to never give up seconds before hitting the button on his remote causing her to be flushed. Chris then says, "I know, we'll all miss her." sarcastically, once again.
|Interactions with||Everyone | Alejandro | Beth | Bridgette | Chris | Duncan | Gwen | Harold | Heather | Lindsay | Scott|
|Other content||Courtney's alliances | Courtney's lawyers | Courtney's personal digital assistant|
|Interactions with||Everyone | Alejandro | Chef | Courtney | Dakota | Duncan | Ella | Ezekiel | Gwen | Heather | Interns | Owen | Sierra | Topher|
|Other content||Chris's cell phone | Larry|