jacksfilms

Douglass launched his main YouTube channel, jacksfilms, on June 26, 2006.[8] His first video was a commercial for a fictional device, the Handy Pen, and featured himself and his family members. Later, he uploaded The WTF Blanket (Snuggie Parody) on January 22, 2009,[7][9][10][11] which has become his most popular video.[12] Many of Douglass' early videos were parodies, often about infomercials, and Apple or Samsung phones.[13][14][15]

In the same month, Douglass visited Electronic Entertainment Expo 2011 (E3 2011) to help Toby Turner film footage for a video. 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 Sideburns Song at VidCon 2012 as well.[16]

On July 1, 2012, jacksfilms reached a total of 100 million video views on his channel. On December 16 the same year, the Fine Brothers released a video titled "Teens React to Jacksfilms".[17] Douglass saw a rapid rise in subscribers, gaining almost 100,000 in the following week. On June 27, 2013, the jacksfilms channel reached 1 million subscribers.[18][19]

In 2014, Douglass' channel jacksfilms was listed on NewMediaRockstars' list of the top 100 YouTube channels, ranked at #54.[20]

On March 21, 2016, Douglass uploaded a first-generation iPhone SE parody in which he mocks the phone for its small screen size.[21][22] In March 2017, Douglass uploaded a video titled Galaxy S8 first look (parody), which has earned more than two million views.[23][24] In September, Douglass made an iPhone X parody, which has over 8 million views (making joking claims including, "The Face ID shoot[s] thousands of lasers straight into your pores. Then it sucks out your soul, much like a Dementor").[25][26][27] Douglass also made several references to Game of Thrones in the videos.[23][27]

In June 2011, Douglass began the series Your Grammar Sucks, mocking internet comments with excessive grammatical and spelling errors. This would become a major recurring series on his channel, and grew to include self-created songs and comedic sketches.

Douglass at VidCon 2014

On January 8, 2014, Douglass launched a new series titled JackAsk, in which he answers viewers' questions in a satirical way. The intro and logo for the series are a reference to the TV series of a similar name, Jackass. The last episode of the original JackAsk was released on October 21, 2020.

On October 21, 2020, Douglass announced on Twitter that he was ending his long-running series JackAsk after 107 episodes. He cited "growing tired of the format",[28] saying that the lack of variety was "killing him".[29] He also announced the end of Your Grammar Sucks on the same day, saying that the two series felt like "obligations" and expressed excitement for the new things to come with their cancellations.[2] Douglass uploaded what he called the final episode of JackAsk on October 26, 2020.[30] However, on May 12, 2021, jacksfilms uploaded a new video entitled JACKASK IS BACKASK!.[31] This was the start of a new blind format of JackAsk.

On June 29, 2017, Douglass celebrated his 11th anniversary on YouTube with a 16-minute compilation of his parodies, music videos and sketches.[32] On July 27, 2017, the day before the release of his Emoji Movie review video, he hit 3 million subscribers.[33] On April 1, 2018, he hit 4 million subscribers. On April 15, 2018, Douglass won the 2018 Shorty Award for YouTuber of the Year, which he accepted while dressed in a Garfield costume.[34]

On January 30, 2017, Douglass referred to The Emoji Movie for the first time in his video How do we fix YouTube? (YIAY #309).[35] Douglass referenced The Emoji Movie frequently in 2017, making a parody of the trailer and selling merchandise of the date of its release, July 28. His videos, "Frame-by-frame analysis of The Emoji Movie Trailer", "THE EMOJI MOVIE - Trailer #2", and "Counting down to The Emoji Movie while spinning 15 fidget spinners and dabbing every 60 seconds" have over 7 million views combined, as of February 2021.[36][37] On July 20, Douglass received a package from the marketing team at Sony Pictures Animation, thanking him for being "the [No. 1] fan of The Emoji Movie", inviting him to the world premiere on July 23, and sending Emoji Movie-related merchandise, including fidget spinners, face masks of Emoji Movie characters, and a plushie of the character Poop.[38] The video in which Douglass unboxed the package and discussed his invitation has received over 4 million views.[39] On July 28, Douglass uploaded a "review" of the film, hinting at the large amount of product placements but acting as if he enjoyed the film. The "review" has received over 7 million views.[40]

In January 2020, he released the song "Twitter for Android",[41] a song made exclusively from tweets that he had put out on Twitter in the past year. He had started this as a joke because people were criticizing him for using an Android smartphone. The first tweet came out on December 30, 2018, and every day after for a year, he would take a screenshot of the chain of tweets, and add a new tweet each day, often saying "Twitter for Android", but sometimes he would tweet other phrases that would be featured in his song. The last tweet was posted on December 31, 2019, an entire year later. This song has received over 2 million views.

On February 3, 2015, Douglass started a daily series on his secondary channel jackisanerd, titled Yesterday I Asked You (YIAY), in which he would ask his viewers a question and then read his favorite answers to the viewers. After 15 days of uploading YIAY videos to his second channel, jackisanerd, he moved the series to his main channel, jacksfilms, and has released episodes on it since. As of February 2022, he has uploaded 600 episodes, making it the series with the most installments on his channel. He also briefly operated a live version of this series known as YIAY LIVE (in which he had live viewers on Twitch compete for the best answer to a given question), which was cancelled due to the large amount of technical difficulties. Many other series, like PewDiePie's LWIAY (Last Week I Asked You), Davie504's SDAIAY (Some Days Ago I Asked You), Aloona Larionova's STTA (Show This To Aloona), Roomie's SIOR (Slap It On Reddit) were inspired by YIAY.

In August 2018, Douglass announced a new series that would take place on Twitch, called YIAY LIVE.[42] This show was a live edition of his popular ongoing series, YIAY, and would have viewers answer his questions in real-time, and he would pick his favorite ones. The viewers would then get to vote for the best answer among those shortlisted ones, and the answer with the most votes would win. There would be 5 different rounds, each with a different format of answering. The winners of the first 4 rounds will be pitted against each other in the final round, and the winner of the final round would receive a code to obtain any merchandise from his official store[43] for free. This show had seven episodes in total, with the last one coming out in October 2018. A special episode was released on April 1, 2019, and was the only YIAY LIVE episode to be released on YouTube.

In May 2020, Douglass uploaded the 500th episode of YIAY, titled "YIAY #500".[44] He previously mentioned that the milestone episode would be 1 hour long,[45] similarly to "YGS #100". It also features many of his YouTuber friends. This video, as of May 2021, has accumulated 2.61 million views.

A live tour for YIAY Live was planned for 2020, but was initially postponed to January 2021,[46] then again later in 2021[47] due to the COVID-19 pandemic.

On October 28, 2020, Douglass created a Kickstarter campaign for a new YIAY-themed board game.[48] It reached its $10,000 goal in just 24 minutes.[49]

On January 4, 2021, Douglass took to his YouTube channel and other social media accounts to announce YIAY TIME: The Game Show, a new YouTube Originals show.[50] It premiered the next day on January 5, 2021, for free on Douglass' YouTube channel.[51] The first episode of the show aired to negative perception, causing Douglass to create a secondary video apologizing and stating that a re-cut and re-edit of the episodes would be put in progress.[52]

On May 7, 2021, Douglass uploaded YGS #128, announcing that the series would be continued and uploaded every Friday. Shortly afterward, Douglass uploaded Jackask #108, announcing that the series would be revived, but under a different format in which he did not read the questions beforehand before answering them. He also does YIAY episodes blindly, with the answers being picked in advance by his Discord moderators, which he refers to ominously as ‘the council’.

On December 29, 2021, Douglass announced on his YouTube channel the creation of a video game by the name of Be Funny NOW!, modeled after YIAY, planned for a release around March 2022, on mobile and on PCs.[53]

On June 13, 2021, Douglass teased an announcement with a tweet, showcasing a silhouetted drawing.[54] The following day, June 14, Douglass officially announced the Erin is the Funny One podcast,[55] revealing that the drawing from the day before was the cover. The podcast was set to be hosted by Douglass himself, as well as his wife, Erin. The name of the podcast is in reference to comments made by fans of the jacksfilms channel in the past, where whenever Erin would make an appearance, many of the comments would say that she should host the channel, and that she was funnier than Douglass.

The podcast's first episode aired on June 28, 2021. The show starts with the "Wine of the Week" segment, in which Douglass or Erin choose a wine, and review it for the audience. This is generally followed by a segment where the hosts talk about the episode's "subject", which is most often a quiz created by either. The last segment is "Horoscopes", where Douglass or Erin come up with horoscopes for the other to read. The segment has shifted from horoscopes for all the zodiac signs to a Mad Libs-type game for only the current season's zodiac sign. The podcast is ongoing, despite a short hiatus from December 2021 to February 2022.

Douglass performing with Toby Turner at VidCon 2012

Douglass' 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".[56][57] Douglass 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, Vincent Cyr, Onision and Stefan Li among others. Douglass has also featured as a voice guest in the asdfmovie series and other sketches by TomSka. On September 26, 2011, Douglass uploaded "Take Off Your Clothes (Like Scarlett Johansson)".[58] On July 23, 2012, he uploaded "The Ray William Johnson Song", which featured ten other YouTube stars including Olga Kay, Felix Kjellberg (PewDiePie) and Steve Kardynal. On September 23, 2012, he uploaded "Your Grammar Sucks #40", which featured YouTube performers including the Fine Brothers and Brock Baker.

Douglass frequently collaborates with animator RageNineteen, on videos such as "KERMIT SINGS",[59] "STORYTIME!",[60] and "Genie",[61] as well as several segments in Your Grammar Sucks #100, Douglass's Short Shorts series, and Royalty Free Christmas Songs. Other animation collaborations include "CARTOON: We wrote anime"[62] with Reality Punch Studios.

Douglass has appeared on the H3 Podcast numerous times, typically accompanied by fellow YouTube creator Erik Hoffstad. A September 2017 episode featuring Douglass gained notable controversy after host Ethan Klein's criticism of PewDiePie's use of the "N-word" during a livestream, receiving over 30 thousand dislikes.[63][64][65][66][67]

Douglass is also known for playing the role of Intern 2 on MyMusic,[68] a defunct show funded by YouTube's $100 million original channel initiative.[69] MyMusic has over 430,000 subscribers and over 48.2 million video views as of September 4, 2018.

In 2014, Douglass began voicing Jimmy, the protagonist in 16-Bit High, an animated series launched by Smosh Games.[70] In October 2015, Douglass portrayed "Pippen" in the film Bob Thunder: Internet Assassin.[71]

Douglass appeared in the 2016 and 2017 editions of YouTube Rewind.[72][73]