Jack went to American University.
Jack launched his main channel, Jacksfilms, on June 26, 2006. He regularly uploads new videos to the channel. On June 27 2013, he achieved 1,000,000 subscribers. over 146 million video views and over 222 video uploads (as of May 19 2013). The first video he uploaded was a commercial for the Handy Pen. The video featured Jack's family members. He later uploaded his most popular video, The WTF Blanket (Snuggie Parody), on January 22, 2009. As of May 8, 2013, the video has earned over 20.8 million views. On July 1, 2012, Jacksfilms achieved 100 million video views. The channel now has 1 million subscribers as of June 27th, 2013.
Many of Jack's films are parodies, often about Apple products and infomercials, and his Your Grammar Sucks series, which has been featured on Post in which he makes fun of incorrect uses of grammar, spelling and punctuation in YouTube and Facebook comments. The most popular episode, which includes cameos by Sean Klitzner and Toby Turner, has garnered over 1 million views. Douglass addresses his fans as "biches", a misspelling of "bitches", which first appeared on the first Your Grammar Sucks. His most successful videos are either parodies, music videos, or sketches; bringing about a new series of videos, abbreviated as 'PMS'. Jack is also known for his Chad series which revolves around a "Delta Sig Delta" frat boy named Chad "Broseph" Huntington. Videos featuring Chad usually features the character giving a review of a movie, while having a buzzword or Chad giving work out advice. His channel also includes a mini-series called "DUBSTEP SOLVES EVERYTHING," a show currently consisting of 3 episodes that make fun of Dubstep music.
On December 16, 2012, the Fine Brothers released a video titled Teens React To Jacksfilms. Douglass saw a rapid rise in subscribers gaining almost 100,000 in the following week.
On February 28, 2013, Jack appeared in an episode of the Fine Brothers show "YouTubers React" called "YouTubers React to Rickroll". He has since appeared in a more recent "Youtubers React" video, titled "YouTubers React to Japanese Commercials". Jack also appears in the most recent "YouTubers React" video, "YouTubers React to Fresh Prince Reunion".
Jack also has four other channels, dubbed Jackisanerd, featuredfridays, SHUTUPDENNIS. He also has a secret channel called "catlvr6969", which has been featured in some main channel videos. The Jacksisanerd channel is mainly used for video blogs and as of February 4, 2013, it has earned over 5 million video views and over 90,000 subscribers. Across his 5 channels, he has over 400 videos. Featured Fridays was originally a series on Jack's main channel before having its own channel for a brief period. The channel has been inactive since March 11, 2011. The channel "SHUTUPDENNIS" has been deemed inactive.</p>
Douglass performing with Toby Turner at VidCon 2012.Jack's relocation to Los Angeles from Maryland] offered opportunities to collaborate with fellow YouTube users and expand his audience. The success of his collaborations with Toby Turner and Sean Klitzner led to the trio being nicknamed "The Sideburns Crew" by their fans. Jack also filmed videos for Los Angeles-based YouTube partner Olga Karavaeva, more commonly referred to as Olga Kay. He has also collaborated with Shane Dawson; and more frequently with Vincent Cyr and Stefan Li among others. Jack was also featured as a voice guest on Thomas Ridgewell's animation asdfmovie4. On September 26, 2011, Jack uploaded Take Off Your Clothes (Like Scarlett Johansson), on July 23, 2012, he uploaded The Ray William Johnson Song which featured ten other YouTube stars including Olga Kay, Felix Kjellberg and Steve Kardynal, and on September 23, 2012, he uploaded Your Grammar Sucks #40 which featured YouTube stars including the Fine Brothers and Brock Baker. On April 19, 2013, Jack uploaded "Your Grammar Sucks #50", which featured many popular YouTubers, such as Anthony Padilla & Ian Hecox of Smosh, Grace Helbig and Felix Kjellberg, better known as PewDiePie.
In June 2011, Douglass visited E3 to help Toby Turner film footage for an E3 Video, then in 2012 Douglass attended E3, this time to promote GREE]. Later that month, during VidCon 2012, Douglass performed a live edition of his Your Grammar Sucks series. Douglass, alongside Toby Turner and Sean Klitzner performed a live version of their iconic Sideburns Song at VidCon 2012 as well.
Jack is also known for playing the role of Intern 2 on MyMusic, a show funded by YouTube's $100 million original channel initiative. MyMusic has over 200,000 subscribers and 13 million video views as of September 12, 2012.