[3] Although only made as a side hobby during free time, their videos were received by a considerable audience of hundreds; this abruptly faded not long after the pair started high school.

[7] Their breakout came with their Nerd Vandals clip going viral, praised by the Huffington Post as the perfect vine,[8] amassing the pair 25,000 followers in a short period of time.

[9] Their vines consisted of 6 second covers of pre-existing songs, also including When This Song Comes On clips made exclusively in the car, short comedy clips featuring the couple as overconcerned parents, nerd alter-egos Eric and Winston, girls in wigs, and more.

[11] By early 2015, they had accumulated over 5 million followers on their shared account and ranked in the top 20 most-followed Viners.

[16][17] In preparation for their debut album, the duo collaborated with Shawn Mendes and Steve Aoki,[18] as well as producers and songwriters Max Martin and Savan Kotecha.

[19] They have also made the Billboard Top Digital Songs List with "Doing It Right", "Tides", "Cold Hearted", "Like That" featuring Skate, "Right Where You Are" and "Wild Life".

[27] On April 17, 2020, member Jack Gilinsky released his debut solo single My Love, featuring Don Toliver.

[28] On September 10, 2020, member Jack Gilinsky dropped his second solo single, "Lose Somebody" featuring Iann Dior.

[29] Both Jacks play instruments and write music,[30] sharing interests across genres including reggae, R&B, pop and hip hop which have influences on their own songs.

[23] In June 2014, after graduating from Omaha Westside High School, the duo recognised the ability to monetize their situation and headed to Los Angeles to work on their headlining tour, DigiTour Jack and Jack coordinated by DigiTour Media.

[32] Alongside this, they also appeared as featured performers at the 2014 INTOUR, an interactive social festival as part of their partnership with FullScreen.

[42][43] They continued their touring contract with DigiTour from June, headlining eight events across the United States, alongside other acts including Demi Lovato and Trevi Moran.

They participated in Ryan Seacrest's 2015 Super Bowl #MakeItHappy campaign, which encourages kindness on the internet and in social media.

[47] They gave a supporting performance at T.J. Martell Foundation's annual New York Family Day event in December 2015.