- December 2 - Charlie is born
- Charlie was arrested for Breaking and Entering
- Charlie was first mentioned in the first video The Old Christmas Rage with Angry Grandpa saying "Charlie ain't sending nothing" and would generally make rare appearances in several videos
- Charlie appears again in My Brother a video posted on KidBehindACamera's channel which shows Michael and Bridgette giving Charlie a pit bull puppy named Pumpkin
- May 10 - Charlie opened his first channel named Charlie Cthulhu
- Charlie was arrested for possession of marijuana, drug paraphernalia, and a "hit and run" accident.
- December 21 - He appears with the rest of the family in KidBehindACamera's video Christmas Party 2014
- Charlie's appearances became more frequent and he moved into his father's new house
- October 8 - Angry Grandpa allowed Charlie to move in and live with him
- October 10 - Charlie starts showing up more in videos
- January 17 - Charlie's first upload on his new YouTube channel named Charlie Badfish, Charlie would reveal lots about himself on this channel
- May 5 - Charlie and Tina Dandrige first meet.
- June 29 - Tina went into Charlie's room where she yelled at him for playing his PS4, all the time he would then yell and scream at the game which made, Angry Grandpa worried. That same day, Charlie had a new nickname of Tina
- August 15 - Charlie opens a new channel named Charlie Chill
- Late August - Early September - Charlie is arrested for Child Support Violations, causing him to serve jail time up until November
- November 27 - Charlie returns to YouTube
- December 3 - Jesse Ridgway (McJuggerNuggets), His father Jeffrey Ridgway Sr.,and Jesse's cameraman Parker Zippel were in South Carolina, Jeff Sr. and Grandpa both destroyed the pool house where Charlie was meant to be moving in. Charlie saw Jesse in Grandpa's house and wanted to attack him, Charlie ran at Jesse, but was soon restrained by Michael and Grandpa, he then forgave Jesse after (Note: This is Jesse's channel so it was possible that Charlie was acting)
- March 17 - Charlie and Tina are in an internet war with each other and are not getting along at all
- June 2 - Charlie gives drugs and alcohol to his 10 year old nephew Jacob and threatened him, following this Charlie is kicked out of the house
- June 4 - Charlie moves out of his father's house and into Michael and Bridgette's pool house
- June 6 - Charlie moves into the pool house
- June 17 - This is when the Ouija Board videos began
- June 29 - Charlie's LSD Incident. The following events were recounted by Michael during an interview with DramaAlert
Earlier in the day, Michael received a call from Chris, a friend of Charlie's who was with the latter at the pool house. Chris told Michael to return home because Charlie had stripped naked and was jumping in the pool and acting weird. Upon arriving home, Michael witnessed a nude Charlie running and dancing around the front yard with a pair of pants on his head. Michael approached Charlie and asked him why he was behaving like this, to which Charlie responded by screaming and growling in his face and threatening to attack him. Michael fled into his house, and Bridgette checked Charlie's Facebook page, where it was discovered that over the course of two hours, he had posted several bizarre updates such as "I'm turning green" and "I'm God". It was also discovered that Charlie had uploaded a number of pornographic videos to his YouTube channel, leading many people into initially believing that his social media had been hacked.
Michael called Kim and told her what happened, and in turn, Kim called the police. By the time the police arrived, Charlie had blacked out and was found laying on the floor of the pool house, which was completely destroyed. When the police approached him, Charlie came to and believed them to be a popular Youtuber named Hagyrants, with whom he was feuding with at the time, and began yelling "I know you're Hagyrants! I know it's you Hagy!". Also, sometime during his rampage, Charlie had used a gas torch and burned one of his fingers to the point where it was described as being completely charred (it is unknown whether he was attempting to burn the pool house down or burn his finger off).
Michael then stated that Charlie admitted to the police that he had taken LSD and drank two bottles of Jack Daniels. Video footage recorded by Michael showed Charlie becoming distressed and refusing to go with the police, as well as blaming Michael for the situation. Charlie also threatened to tell people that Bridgette was having sex with her cousin and was an incestuous lesbian, Michael has sex with his dog, and Angry Grandpa is a child molester (although this was not shown in the clip). Eventually, Charlie relented and was seen being wheeled away on a gurney to be hospitalized for his finger burn as was a brief mental evaluation.
Later that day, Charlie was discharged from the hospital and caught an Uber back to the house, where Michael was inside his house editing a vlog about the incident and Bridgette and Doug were in the pool house. Michael said he heard screaming and witnessed Charlie hit Bridgette twice in the face. An enraged Michael ran outside to beat him up, but Charlie threatened him with a piece of broken mirror that he retrieved from the pool house. Michael and Bridgette ran back to the house to call the police, and a short video recorded by Bridgette showed Charlie advancing towards them and calling Bridgette derogatory names. Also, before Bridgette began recording, Charlie reiterated the accusations from earlier into Bridgette's phone, believing that she had already started recording.
The police showed up for a second time, and Charlie tried to tell them that Michael and Bridgette destroyed the pool house, but they were the same officers who witnessed him do it earlier. He also told them that any drugs found in the pool house belonged to Michael, and he also denied hitting Bridgette. The police didn't believe Charlie and arrested him, and Michael said that he will not be bailing Charlie out, but instead pressing any charges he can.
- June 30 - Immediately after the incident Charlie was disowned by The Green Family
- July 1 - Michael revealed that he, Jennifer, Doug, and Chris allowed Charlie to check into an Extended Stay hotel in North Charleston until his court date. On that same day, Kim posted on Facebook that when she was a child, Charlie and one of his friends tried to rape her. Upon finding this out, Michael, Bridgette, Jennifer, Kim, and Angry Grandpa all agreed that Charlie was officially going to be disowned and permanently dead to the Green family and that he will be banned from all family gatherings, holidays, important events, etc for life, thus he will be banned from Angry Grandpa's house and Michael's house.
- July 2 - Charlie was interviewed by DramaAlert. He continued to deny hitting Bridgette
- July 6 - Isaac (a close friend of Michael's) went down to Charlie's hotel to confront him about the threats Charlie made to Isaac's family. Charlie called the cops
- July 7 - Charlie checked into rehab, he said he'd be back within 45 days. On August 8th, 2017, Charlie apparently checked out of rehab. The next day, he showed us his certificate and white chip of completion proving he did go to rehab and also revealed who he was currently living with.
- August 15 - Michael and Bridgette dropped all charges against Charlie, deciding not to deal with the situation any longer.
- August 17 - Charlie posted a video with Michael, showing that the two were back on better terms
- September 24 - Charlie started a huge attack rant on Twitter to Isaac. He stated that he'd rape his dead grandmother and other malicious things. He made two Twitter videos and a YouTube video giving Isaac permission to come to "Charlie's house". All this lead to his YouTube channel receiving a second strike and a ban on Twitter. It's assumed he was drunk. Charlie would make another twitter account a few days later. Much later, the person Charlie was living with released videos of Charlie (on Sep. 24th) threatening to rape Isaac's wife and kids, and saying that he would go to his fathers grave and shit on it. Soon after this event, Michael cut all ties with Charlie and changed his number
- October 5 - Charlie's roommate revealed that Charlie was kicked out. She also revealed lots about Charlie stating that during the Mayweather fight back in August, Charlie relapsed and began drinking again. She also said that Charlie blackmailed her, threatening to tell people that they slept together despite her being married. By the second week of October, Charlie was homeless and sleeping in a tent
- October 12 - Charlie relocated to Florida
- October 14 - Charlie made an attack on Michael, stating how Michael never told Isaac to stop making videos exposing Charlie, saying how "money doesn't buy love".
- October 29 - Four months after the LSD incident, Charlie's channel had porn uploaded to it again, and his header name changed from Charlie Chill to "Child Molester". This would lead to a third channel strike, making his channel terminated.
- October 30 - Charlie would create another channel called "Charlie Again" (later renamed to Charlie Travels).
- October 31 - November 2 - Charlie would make attacks on Michael and Angry Grandpa (despite Grandpa being in the hospital) saying how Michael was selfish for not inviting him to say goodbye to his father. Michael explained on Twitter and YouTube that what Charlie was saying was completely false. Michael claimed that he called Kim first, then had a third party reach out to Charlie to have him say goodbye. Angry Grandpa reportedly told Kim to not have Charlie come to see him.
- November 3 - Tina made a video to Charlie, stating that a friend of hers can get Charlie down there to say his goodbyes to Angry Grandpa in case that it is the end. Tina didn't like the idea but felt it would've haunted Charlie for life if he couldn't do so. The same day, Charlie stated he made it back to South Carolina. He called Angry Grandpa, and Angry Grandpa reportedly stated: "I love you, you do you, live your life, but I don't want you here". Later that day, Charlie posted on Facebook stating that he "wishes his dad would die already".
- November 4 - Isaac went down to South Carolina to help Michael and the family. Charlie apparently found out and made more threats to Isaac. Isaac showed up and went face-to-face with Charlie. Isaac begged Charlie to punch him first. Instead, Charlie went into the hotel he was staying at and called the police. According to both Isaac and Charlie, Charlie was later kicked out of the hotel for causing trouble and finding out from Isaac the threats Charlie made on Sep. 24th
- November 5 - November 11 - Charlie would keep trying to spread rumors about Michael and how he "fakes videos" but these were all shot down by Michael.
- December 10 - Angry Grandpa passed away. Charlie was the only one of his four children not at his bedside as Angry Grandpa died
- December 14 - December 16 - Charlie and Mike reunited once again and put their differences aside for Angry Grandpa's memorial. And it seems Charlie had been getting back on a better track.
- January 8 - Isaac and Charlie patched up their beef as well, as Isaac was seeing a positive change in Charlie, he donated $20.00 to Charlie's stream and wished him luck in the future, putting the two on better terms. Isaac, Michael and Charlie even had a plan to be on vlog together someday.
- January 28 - Charlie started making various threats towards Tina, stating that he has people to go and beat her up. After the storm calmed, Isaac & Michael revealed that Charlie may have been drunk once again.
- January 29 - Michael announced in a video that he has once again cut ties with Charlie, this time permanently. Isaac also announced how Charlie was back to threatening Isaac, making him an enemy once again
- January 30 - Early February - Charlie started making threats to kill Michael on Twitter, No one knows where this is headed, but Michael is implying that he is defending himself if the situation actually gets real bad.
- February 12 - February 14 - Charlie would once again drunkenly rant on Twitter and even attacked Boogie2988. These actions ended up getting him temporarily banned.
- February 15 - Charlie live-streamed himself threatening to go to Michael's house and kill him along with Bridgette. This lead many to call the cops on him.
- February 16 - Michael and Bridgette revealed in a vlog that they have filed a police report against Charlie for his threats the previous night and told Charlie to leave them alone and go live his life. This would be the last time Michael and Bridgette mentioned Charlie in a vlog until a vlog posted on October 12, 2018, when Michael briefly talked about the Charlie Chill LSD Incident that happened the previous year
- February 22 - Charlie's Charlie Travelz channel was terminated for violating Youtube's policy prohibiting content designed to bully or threaten. On or about February 23rd, 2018, Charlie launched a new channel with his new superfan girlfriend Erica Roland. The EricaCharlie Experience was quickly renamed to Travels Together.
- March 19 - Travels Together was terminated by YouTube for Terms of Service violations. But a fourth YouTube channel known as Checking In Together was created by Charlie and Erica on the same day. It was then later changed to The Outsiders, then The Outsiderz.
- August 13 - Charlie and Erica's The Outsiderz channel was terminated for violating Youtube's policy prohibiting content designed to bully or threaten. On August 14th, 2018, Charlie and Erica created a fifth YouTube channel known as The Side Project. But it was terminated by YouTube for a Terms of Service violation within a day after its creation.
- August 15 - Charlie announced that he and Erica were creating a website where all of his future vlogs would go, stating "They can't take us down there."
- August 21 - Charlie's first website was launched as well a sixth YouTube channel named "Travelz Together" About a year later, the channel was terminated by Youtube.
- August 28 - Charlie took to Twitch and threatened to kill Michael, Isaac & Tina again. During that same stream, he also flashed his private parts. Erica was at work during this and people were warning her that Charlie was drunk, Isaac himself phoned her to tell her and she was quoted as saying "I'm tired of babysitting." Later that night, Erica got home and posted a selfie on Twitter with Charlie passed out drunk in the background saying "We are okay". Charlie's Twitch channel was subsequently terminated, and Michael responded on Twitter by announcing that he has contacted the FBI and advised people to remind Charlie's followers that they are defending someone who tried to rape his sisters.
- September 16 - Charlie announced on Facebook that he created a new page titled, "TravelzTogether".
- September 18 - Charlie's twitter account got suspended for all the vulgar tweets he made against Isaac's family.
- February - Charlie made a new account on Twitter named, "charlieboy".
- March 10 - Charlie tweeted that he and Erica are temporarily separating.
- March 11 - Charlie announced in a tweet that his half-sister Dawn (Angry Grandpa's daughter from his first marriage) has offered to let him stay in her home in Alabama until he and Erica work things out.
- March 15 - Charlie said in a video on Facebook that he tried to reach out to Michael and Bridgette through private messaging on Twitter, but when they saw the messages, they immediately blocked him without saying a word to him.
- March 18 - Charlie ranted about Michael, Isaac, and Jennifer by posting numerous tweets about them.
- March 19 - Charlie got into a fight with Dawn and her sister (not one of Angry Grandpa's children) on Twitter and announced that he was leaving Alabama to return to North Carolina so that he can get back together with Erica. Dawn defended Charlie in a tweet stating that she is not kicking him out and letting anyone influence their relationship as half-siblings. Charlie was suspended once again on Twitter afterwards.
- October 30 - Charlie and Erica's channel: The Outsiderz was terminated for a violation of YouTube's terms of services
- March - May - Charles countinues harrasing and bullying people online
- April 5 - Charlie Goes live with Doug West on livestreams
- Sometime in Mid-May - Travelz Together is terminated
- Charlie makes a new channel with the same title
- May 13 - Charlie got into an argument with Nick Welsh (Doug’s nephew) on Facebook and made threats about him and his children