Jack Douglass

Douglass was born in Columbia, Maryland, on June 30, 1988, and is primarily of Irish ancestry. He has two older sisters. Douglass went to elementary school and middle school in Maryland. During high school, he started to develop a love for music. He then began to play the French horn as well as the piano.

In May 2006, during his senior year of high school, he was given the task of making a video about all the books he had read during the year. He and his friends decided to film a series of short videos that made fun of books such as Beowulf and All the King's Men. After making these sketches, he decided that he wanted to make films to a greater extent. By the next month, he had begun using YouTube and had started to upload videos.

Douglass launched his main YouTube channel, jacksfilms, on June 26, 2006. 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, which has become his most popular video. Many of Douglass' early videos were parodies, often about infomercials and Apple products. Douglass's earliest content also included various parodies about smartphones from Apple and Samsung, first starting with a parody of the iPhone 4S.

In June 2011, Douglass began the series Your Grammar Sucks, primarily featuring him reading user-submitted comments with grammatical and spelling errors. This would become a major recurring series on his channel, and grew to include self-created songs and comedic sketches. In October 2020, Douglass announced that Your Grammar Sucks will end at the end of 2020 after 130 episodes.

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". 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)". 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. On September 23, 2012, he uploaded "Your Grammar Sucks #40", which featured YouTube performers including the Fine Brothers and Brock Baker.

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

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". 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.

In 2014, Douglass' channel jacksfilms was listed on NewMediaRockstars' list of the top 100 YouTube channels, ranked at #54. On November 20, 2015, the same day as "Your Grammar Sucks 100" released, Douglass hit 2 million subscribers.

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 completed series contains 107 episodes, he officially posted the last JackAsk on the 27th of October 2020.

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

On February 3, 2015, Douglass started a daily series on his secondary channel jackisanerd, titled Yesterday I Asked You (YIAY), in which he asks his viewers a question and reads 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 September 2020, he has uploaded 522 episodes, making it the biggest series on his channel. He also briefly operated a live version of this series known as YIAY LIVE (in which he had live viewers compete for the best answer to a given question). There also other versions of YIAY, 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), and many others. This type of all the formats are called Last time I asked you (LTIAY)

On November 20, 2015, Douglass started a new series on the Regal Cinemas YouTube channel named Jack Talks Trailers, in which he gives a brief recap of new film trailers that are released within the past week. At the end of each episode, Douglass reads the opinions of people's thoughts about a specific trailer shown in the episode. Douglass' last video for Regal was uploaded on July 29, 2016.

On March 21, 2016, Douglass uploaded a first-generation iPhone SE parody in which he mocks the phone for the small screen size. In March 2017, Douglass uploaded a video titled Galaxy S8 first look (parody), which has earned more than two million views. In September, Douglass made an iPhone X parody, which has over 3 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"). Douglass also made several references to Game of Thrones in the videos.

Douglass appeared in the 2016 and 2017 editions of YouTube Rewind. He also attended E3 2017, where he filmed a sketch video; and E3 2018, where he filmed an episode of YIAY. On June 29, 2017, Douglass celebrated his 11th anniversary on YouTube with a 16-minute compilation of his parodies, music videos and sketches. On July 27, 2017, the day before the release of his Emoji Movie review video, he hit 3 million subscribers. 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.

On January 30, 2017, Douglass referred to The Emoji Movie for the first time in his video How do we fix YouTube? (YIAY #309). 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 5 million views combined, as of November 2017. 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 Poop. The video in which Douglass unboxed the package and discussed his invitation has received over 2 million views. On July 28, Douglass uploaded a review of the film, hinting at the large amounts of product placement but generally acting as if he enjoyed the film. The review has received over 6 million views.

On January 1, 2017, Douglass became engaged to his longtime partner Erin Breslin. The couple married on April 21, 2018. Douglass owns three American Eskimo dogs named Klondike, Sundae and Chipwich. Their oldest dog, Klondike, inspired Douglass to create a new line of merchandise named after her. A semi-satirical dig at Logan Paul's "Be a Maverick" clothing line, the line features images of the Eskimo dog.

In August 2018, Douglass announced a new series that would take place on Twitch, called YIAY LIVE. 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 for free. This show carried out seven episodes in total, with the last one coming out in October 2018. A special episode was held on April 1, 2019, and this was the only YIAY LIVE episode that aired on YouTube.

In March 2019, Douglass posted a video where he asked people on the street, "Can ANYONE name a single character from the movie Avatar?" Only one respondent was able to name a character from the film. In May, Douglass posted a video titled "Watch Endgame. Beat Avatar.", in which he urged the viewers to watch Avengers: Endgame and make the film take Avatar's title as "The top-grossing film of all time".

In January 2020, he made the song "Twitter for Android", 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 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 of tweets later. This song has received over 2 million views.

In May 2020, Douglass uploaded the 500th episode of YIAY, titled "YIAY #500". He previously mentioned that the milestone episode would be 1 hour long, similarly to "YGS #100". It also features many of his Youtuber friends. This video, as of October 2020, has accumulated 2.21 million views.

In August 2020, Douglass uploaded an interactive YouTube video, titled "CHOOSE YOUR OWN APOLOGY VIDEO". It has 32 different endings and 2 different scenarios.

On October 21, 2020, Douglass announced on Twitter that he was ending his long-running series JackAsk after 107 episodes after growing tired of the format, saying that the lack of variety was "killing him". 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. The final episode of JackAsk was uploaded on October 26, 2020.

On October 28, 2020, Douglass created a Kickstarter campaign for a new YIAY-themed board game. It reached its $10,000 goal in just 27 minutes.