In Karma Chameleon, Jimmy pushed Sean Cameron into a locker when he found out that he was going on a date with Ashley Kerwin. Craig broke up the fight before it could go any further and asked Sean if he was alright. In spite of the circumstances of their first on screen meeting, Craig and Jimmy eventually became very close friends.
In Drive, Craig invited Jimmy, Sean, Marco Del Rossi and Spinner Mason to his house, as his stepfather Joey Jeremiah was away for the weekend. However, Jimmy was angry that Sean was invited and did not attend.
In Take My Breath Away, Craig confided in Jimmy and Spinner that his date with Manny Santos the previous night had been "bizarre", that she was too immature, and that she reminded him of his five-year-old half-sister Angela Jeremiah. Both Jimmy and Spinner thought that was weird.
In Fight for Your Right, both Craig and Marco were impressed by the new clothes that Jimmy's father Jermaine Brooks had bought him as a belated birthday present. Craig asked him if he had won the lottery while Marco wondered if he had left anything on the racks.
In Tears Are Not Enough (2), Jimmy and Marco expressed their sympathy to Craig after his father, Albert Manning, died in a car accident. When they noticed that his and Mr Simpson's stories did not match, Craig alarmed them by making a joke about his father's death.
Season 4In Time Stands Still (2), Craig walked down the hall to see Jimmy lying on the floor, after he had been shot in the back by Rick Murray. He later told Joey that Jimmy was shot and was in the hospital. That night, Craig, Joey, Angela Jeremiah and Caitlin Ryan watched the coverage of the shooting on the news and Craig began to cry.
Before Downtown Sasquatch's recording session in Neutron Dance, Marco sadly told Craig that they would sound better if Jimmy could play with them. Craig said, "I wish he could too." While visiting Jimmy at the hospital, Craig told him that Ashley had begun advising the band on their sound but that they were just friends and they would never get back together. However, Jimmy could tell that Craig still had feelings for her. When Jimmy described himself as being "crippled," Craig was visibly upset and told him not to say that about himself.
In Voices Carry (1), Craig skipped a study period to visit Jimmy in the hospital. They discussed his relationship with Ashley, whom Craig believed was on the verge of dumping him.
While experiencing a euphoric high as a result of his bipolar disorder in Voices Carry (2), Craig again visited Jimmy in hospital and told him that Ashley agreed to marry him. Jimmy was surprised, telling him that, at sixteen, they were too young and that they should think about finishing high school and getting jobs before marriage. He concerned by Craig's odd behaviour, asking him if he was drunk, high or just crazy. Craig became angry and told Jimmy that he should be happy for him before leaving.
After Jimmy was paralyzed from the waist down during the school shooting, Craig and Marco were especially supportive during his recovery. In Secret (2), Jimmy was anxious to return home after being in hospital for several months and was looking forward to seeing a Kid Elrick concert with Craig and Marco. However, his father Jermaine Brooks told him that the house would not be ready for another week and that he would have to stay in hospital for the time being. Not willing to accept this, Jimmy convinced Craig and Marco to break him out of the hospital the next day so that they could go and see the concert together. Jimmy and Marco wore black hoodies for their escape while Craig entered the hospital wearing a fedora and trenchcoat. Craig distracted the nurse on duty by continually asking for a fictional German doctor and then pretended to be extremely ill and, when the nurse left to get him help, he, Jimmy and Marco made their escape.
While it was difficult for Jimmy to navigate his way around the club where Kid Elrick was performing, he did extremely well and he and his two friends were in the front row for the entire concert. As Craig and Marco sneaked Jimmy back into the hospital that night, they excitedly discussed the concert. When Craig commented that they were so close to Kid Elrick that he was practically sweating on them, Marco said, "I am never gonna shower." A confused Craig laughed at his best friend's odd comment while Jimmy said that he would smell like Jack Daniel's if he did not wash. However, the three boys found Jimmy's father there waiting for him. Jimmy convinced him that he was ready to come home but that his father need to be ready. Mr Brooks agreed to collect Jimmy the next morning and bring him home.
In Eye of the Tiger, Craig was among the many students present to greet Jimmy at the front of Degrassi when he returned to school after three months in the hospital. The next day, after it became common knowledge that Spinner was responsible for dumping the paint on Rick, he and Marco confronted him. Craig told him to stay away from Jimmy while Marco told him that he was no longer invited to Jimmy's welcome back party at Craig's house. However, after getting drunk with Jay Hogart, Spinner showed up anyway. Craig angrily told him to leave. Spinner begged for forgiveness but Jimmy ignored him, telling Craig to continue playing karaoke as they had been doing before Spinner arrived. Spinner left but Marco saw that he took his keys with him and realised that he was going to try and kill himself. He and Craig attempted to stop Spinner from driving away but Jimmy moved himself in front of the car. He told Jimmy that he was not going to stop him as he was dead to him already. Craig then confiscated Spinner's keys.
After Craig got into a fight with Joey, who would not let him go to England to be with Ashley for the summer, in Goin' Down the Road (1), Craig met Jimmy in the mall and played him the instrumentals for the song that he was writing for Kevin Smith's film Jay and Silent Bob Go Canadian, Eh!. When he told Jimmy that he still needed lyrics, Jimmy suggested, "Ashley, please don't go. Ashley, please don't leave me. Don't fall in love with an ugly limey." By this time, Jimmy was aware that Craig was bipolar as he did not object to Joey referring to his condition in front of him.
In Venus (1), when Jimmy, Craig, Ellie, Paige and Hazel saw that Spinner was back at Degrassi, they avoided him. The next day, Jimmy attended Craig's surprise 17th birthday at the Dot.
In Venus (2), Jimmy and Craig saw the video of Manny Santos drunkenly flashing her breasts on camera, Jimmy commented "Manny Santos, my how you've grown." Craig told him to shut up as it was not funny. They later had lunch with Marco in the cafeteria.
In I Still Haven't Found What I'm Looking For, Craig was disappointed that Jimmy was leaving the band to try out for a wheelchair basketball team. He told Jimmy that they would miss him being in the band but wished him good luck.
In Redemption Song, Craig congratulated Jimmy when Ms. Hatzilakos announced that he had been commissioned to paint a mural commemorating the school shooting. He later helped Jimmy paint it and was shocked when Hazel threw a can of paint over Jimmy as he had included Ellie in the mural.
By Together Forever, Jimmy had rejoined the band but it broke up shortly afterwards when Craig moved to Vancouver to pursue his solo music career. He was there to say goodbye to Craig before he left.
In What's It Feel Like to Be a Ghost? (1), when Craig returned to Toronto, Jimmy came to Marco and Ellie's house to welcome him home and listened to him sing his new song, "Drowning".
In It's Tricky, Jimmy was delighted that Craig gave him a shout out in the acknowledgements of his album Of Two Minds. However, he became annoyed when he found out that Craig had used one of Ashley's songs, "My Window", without crediting her.
In Bust a Move (2), it was revealed that Craig was the mystery guest at the Purple Dragon Mystery Concert in Smithdale University. He was glad that so many of his old friends were in the audience. Jimmy realised that Ashley had known that it would be Craig. She told him that Craig emailed her after she and Jimmy broke up and asked her to go on tour with him in Europe. Craig said that the album would not have been possible with Ashley, whom he said had always been his friend and inspiration. He invited her up on stage and they performed "My Window" together.
- (Craig shows Jimmy and Marco his science exam in which he got an A+)
Jimmy: "A! That's my man."
Marco: "Wow. That's amazing, buddy."
Craig: "Yeah, my dad actually did something worthwhile for me. He was a good study partner."
Jimmy: "Look we're really sorry to hear about your dad, man."
Marco: "Yeah. So you okay?"
Craig: "Guys, I'm fine. Hey, I'm the lucky one. My dad died. I, I walked away with a scratch."
Marco: "I thought you weren't in the car..."
Craig: "Friday night, we're like speeding down the highway, my dad's mad and he won't slow down. Ahead there's a rig. I see it, my dad doesn't and we hit...hard."
(Jimmy and Marco are shocked. Craig laughs)
Craig: "Guys, I was at Joey's when it happened! I had you going though." - Tears Are Not Enough (2)
- Craig: "I got news! Big news! You ready?"
(Craig takes his trousers off)
Jimmy: "What?! No. Hold on!"
Craig: "First wedding I ever went to was my mom's to Joey. Spike and Simpson's was number two. Ashley's dad makes three. See I want to get my practice down, you know? Get things right before my own wedding."
Jimmy: "Okay, you got time for that."
Craig: "I asked Ashley and she said yes."
Jimmy: "You're actually getting married?"
Craig: "Congratulations! Anytime..."
Jimmy: "You're sixteen. Don't you want to wait for I don't know, graduation? Maybe an occupation?"
(Craig is not listening and is trying to button his cuffs)
Craig: "Could you do this up? Please?"
Jimmy: "Are you drunk? Are you high? Or are you just out of your mind?"
Craig: "I love her!"
Jimmy: "Okay, that still doesn't explain what's up with you or this insane idea!"
Craig: "Maybe you should just think about it and try to understand. I don't know, be happy for me!" - Voices Carry (2)
- They were both born in September: Jimmy in 1987 and Craig in 1988.
- They both dated Ashley Kerwin.
- She dumped each of them on his birthday: Jimmy on his 14th birthday in Coming of Age and Craig on his 17th birthday in Venus (1).
- Although Ashley's mother Kate Kerwin was very fond of Jimmy, she disliked Craig as he cheated on Ashley with Manny Santos.
- While Craig had sex with Ashley in Voices Carry (1), Jimmy tried and failed to do so twice, in The Mating Game and Can't Hardly Wait.
- They were both close friends with Ellie Nash, Marco Del Rossi and Spinner Mason. However, Craig ended his friendship with Spinner after learning about Spinner's indirect role in the school shooting in Eye of the Tiger and it was never made clear if he ever forgave him.
- They were involved in a love triangle with Ellie. Jimmy had an unrequited crush on Ellie while Ellie had an initially unrequited crush on Craig. While Ellie's feelings for Craig were eventually returned, Jimmy's feelings for Ellie were not. Craig never found out that Jimmy had feelings for Ellie.
- They were both acquainted with Ellie for several years before becoming friends with her. Both of them came to consider Ellie to be one of their best friends.
- They were seen in the Season 5 opening credits together.
- Neither of them graduated in the Class of 2006: Craig dropped out in Together Forever and Jimmy was held back in High Fidelity (2). He graduated as part of the Class of 2007 in We Built This City.
- They were both big fans of Kid Elrick.
- Like Ellie and Paige Michalchuk, neither Jimmy nor Craig had any problem with the fact that Marco was gay after he first came out. This was in stark contrast to Spinner's initial homophobia.
- Jimmy had a conflict with Craig's former friend Sean Cameron but it was eventually resolved.
- They were both founding members of Downtown Sasquatch.
- As revealed in Goin' Down the Road (1), Craig trusted Jimmy enough to tell him that he was bipolar.
- Craig mentioned Jimmy in the acknowledgements of his album Of Two Minds.
- They were both members of Archie Simpson's Grade 9 homeroom class 9F from 2002 to 2003.
- Jimmy's ex-girlfriend Hazel Aden thought that Craig was cute.