- July: ThatGuyWithTheGlasses showed up on YouTube and started the 5 Second Movies and The Nostalgia Critic shows.
- December: Version 1 of the site appeared with minor information.
- April 3rd:ThatGuyWithTheGlasses.com officially launched and all 5 second movies and Nostalgia Critic episodes were gradually moved over to the site. The following sketches were added in the ensuing weeks: The Bjork Show, Cheerios 2, How I Quit My Job and Aristocrats. Mike Michaud is instated as administrator of the site.
- April 18 and 19th: First Nostalgia Critic rants against The Nerd.
- April 20th: First Nostalgia Critic episode on the site: Pokémon the First Movie.
- Doug Walker issued his welcome message for the site, welcoming the people.
- April 21st: Site trailer launched. Version 2 of the site launched.TGWTG.com is born!
- April 27th The Wizard Rant against The Nerd.
- May 11th: Bum Reviews aired its first episode with a review of "Speed Racer".
- May 22nd: The Other Guy began writing articles with a review of "Iron Man".
- May 28th: The Last Angry Geek's comic reviews began with a look at "ROM: Space Knight". See The Last Angry Geek's Articles for more.
- July 6th: Bhargav Dronamraju appeared as "Ma-ti" in the Nostalgia Critic "Captain Planet" review.
- June 10th: Premium site content launched.
- June 13th: Ask That Guy With the Glasses aired its first episode.
- June 15th: The Nerd responds.
- June 16th: Videos are taken off of Doug's YouTube channels. Doug responds with a special episode of Askthatguy stating that he was going to take them off anyway.
- June 18th:Channel Awesome Youtube was created by Welshy. Eventually, this became the official Youtube channel for Channel Awesome.
- June 20th and 22nd: The Bum appeared on AskThatGuy.
- June 24th:That Dude In the Suede's first 5 Second movie, "Neon Genesis: Evangelion".
- June 25th: Lori Prince Live premiered.
- June 30th: Handsome Tom interviews Doug.
- July 20th: Animenia by That Dude In the Suede premiered with the Top 11 Greatest Animé theme songs.
- Film Brain started his series of 5 second videos with "Dumb and Dumber" in 5 seconds.
- July 21st: Film Brain wrote an article where he introduced himself and then went on to create more articles reviewing movies. See Film Brain's Articles for more.
- July 22nd: The Spoony One's reviews appeared on the site.
- August 1st: The Spoony One began The Most Awesome Thing. He looked at "Black Summer".
- August 3rd: AMV Heaven by That Dude in the Suede aired.
- The Nostalgia Critic reviewed the game, "Bebe's Kids".
- August 10th: The Search for the Nostalgia Chick began.
- August 13th: ThatAussieGuy's show Riz's Rave Reviews aired for the first time with "The Bourne Conspiracy".
- August 15th: GSYMDK by Benzaie premiered with a look at the soundtrack to Lethal Weapon.
- Michaud announced the first Best of Blogs contest where winners would get a spot on the site!
- August 17th: Forums were launched.
- August 22nd: Chat room created.
- August 29th: The Search for the Nostalgia Chick contest ended with five finalists: MarzGurl, TheDudette, ThatChickWithTheGoggles, Lauren and Drew. Also, the winners of the first Best of Blogs contests were added to the site: Coldguy, Rollo T and Bennett The Sage.
- September 5th: Coldguy began writing articles. His first look was at "MAGfest". See Coldguy's Articles.
- September 9th: ThatChickWithTheGoggles began The Games I Grew Up On with a look at "Jill of the Jungle".
- September 15th:TheDudette is crowned the The Nostalgia Chick. Fellow runners up MarzGurl and ThatChickWithTheGoggles were also given spots on the site.
- September 16th: The Nostalgia Chick's first episode aired with a look at "Pocahontus".
- September 17th: The Users of TGWTG.com in 5 Seconds Contest began.
- September 23rd: The Aussie Critic released with ThatAussieGuy as host. He reviewed "Crocodile Dundee".
- The Spoony One began his review of "Final Fantasy VIII".
- ThatChickWithTheGoggles released Quickies. Her first look was at "Katamari Damacy".
- September 24th: Nostalgia Critic/Nerd Last Showdown.
- Geek-lover.com interviews Doug.
- Cory Lemay interviews Doug.
- September 26th: Rollo T began his articles called Hollywood Genocide.
- October 1st: MarzGurl created an intro video with a sketch.
- October 5th: Benzaie's Top 5 began with a look at the The Top Five Worst Genesis Movie Games and his Five Second Video Games began with a look at "Teenage Mutant Ninja Turtles" for the NES.
- October 9th: AskThatGuy issued a contest to find the zaniest answers to five questions he selected.
- October 10th: The Nerd vs Nostalgia Critic: The Final Battle
- October 13th: Video showing the Users of TGWTG.com in 5 seconds was released.
- October 16th:Transmission Awesome, the official podcast for the site began as hosted by HopwithinChaos, Rollo T and Coldguy. With them was ThatAussieGuy.
- October 17th: Internet Superstar interviews Doug.
- October 20th: Little Miss Gamer and PBC Productions began appearing on the site with a look at "High Compatibility".
- October 21st: The first Nostalgia Critic Halloween special: NC vs Teddy Ruxpin.
- October 25th: The Nerd vs Nostalgia Critic retrospective aired.
- October 27th: Riz's Rewind Rave began with a review of Mighty Final Fight.
- The Spoony One began his vlogs and reviewed "Dead Space".
- October 30th: Benzaie premiered FAQ You! with a look at "Infinite Discovery".
- November 16th: Dr. Gonzo began writing articles with a look at dads and their infatuation with high scores. See Dr. Gonzo's Articles for more.
- Columbia College Q&A
- November 17th: Phelous started his reviews on the site. First up was "mac and me".
- November 21st: MarzGurl started a two part look at the history of animation.
- November 23rd: Lion King Rifftrax.
- November 29th: Linkara's Atop the Fourth Wall began with a look at the top 15 WTF moments in comics.
- December 3rd: Trailer Trash Quantum of Solace aired.
- December 20th: Make 'em Laugh Commercial.
- December 24th: Happy Holidays message from the staff of the website.