jacksfilms

Douglass launched his main YouTube channel jacksfilms on June 27, 2006.[8] He uploaded "The WTF Blanket (Snuggie Parody)" on January 22, 2009,[4][9][10][11] which is his most-viewed video as of October 2023, amassing over 25.7 million views.[12][13][14] Many of Douglass' early videos were parodies, often about infomercials, and Apple or Samsung phones.[15][16][17]

On June 20, 2011, Douglass began the series Your Grammar Sucks, mocking internet comments with excessive grammatical and spelling errors. Your Grammar Sucks would ultimately be the catalyst that jumpstarted Douglass' popularity on YouTube, and on June 27, 2013, the jacksfilms channel reached 1 million subscribers; this sits at a combined 6.07 million across his YouTube channels as of October 2023.[18] In 2014, Douglass' channel jacksfilms was listed on NewMediaRockstars' list of the top 100 YouTube channels, ranked at #54.[19]

Douglass at VidCon 2014

Logo used for the web series YIAY since 2015

Douglass created the "Yesterday, I Asked You" series in 2015, which involves him asking various questions to his audience and reading his favorite responses.[20] Throughout 2016 and 2017, Douglass released a series of phone commercial parodies, on the first-generation iPhone SE,[21] Galaxy S8,[22] and iPhone X.[23][24] These parodies received media attention from CNET[24][21] and Kotaku.[21] On April 15, 2018, Douglass won the 2018 Shorty Award for YouTuber of the Year.[25]

After Douglass made videos poking fun at The Emoji Movie, he received a package from the film's marketing team on July 20, 2017, thanking him for being "the [No. 1] fan of The Emoji Movie".[26] They invited him to the world premiere on July 23, and sent Emoji Movie–related merchandise.[26]

Douglass published The YIAY Book on December 2017, collecting 50 previously asked questions on YIAY with his own answer.[27] He later launched a Kickstarter campaign for "YIAY: The Board Game" on October 28, 2020,[28][29] transforming the YIAY video formats into a board game which combined the Cards Against Humanity format with YIAY-themed questions.[30][31][32][33]

On January 4, 2021, Douglass announced YIAY TIME: The Game Show, a new YouTube Originals show.[34] It premiered the next day on January 5, 2021, for free on Douglass's YouTube channel.[35] On May 17, 2022, Douglass and Galvanic Games released Be Funny Now!, a free-to-play online party game for iOS, Android, and Steam, where players compete to answer prompts in the funniest way possible.[36] On November 8, 2022, the game received a 2.0 update, which introduced a revamped voting system.[37]

In 2022 and 2023, Douglass criticized YouTuber Alia "Lia" Shelesh, better known online as SSSniperWolf, over her reaction video content, calling out her use of viral videos from TikTok, as she did not ask for permission to use the videos and often failed to provide credit to the original creators, and alleged that her commentary was not sufficiently transformative to qualify as fair use. Douglass created the channel JJJacksfilms, and began uploading videos reacting to Shelesh's content.[38] In response, Shelesh made several social media posts accusing Douglass of sexism and stealing her content.[39]

On October 14, 2023, Douglass accused Shelesh of stalking and doxxing after she posted information about Douglass' residence online, including recording a video of herself outside of his home on Instagram.[40][41][42] About a week later, YouTube temporarily demonetized Shelesh's entire channel, writing: "off-platform actions that put others’ personal safety at risk harm our community & the behavior on both sides isn’t what we want on YT. Hoping everyone helps move this convo to a better place."[43][44]

On October 20, 2023, Shelesh issued an official apology to Douglass, as well as to her fanbase, and to the wider YouTube community, in the form of an Twitter post, which garnered negative reception.[45][46]