[2] Drew Gooden was born on October 26, 1993,[P 1] in North Carolina, and has lived in Orlando, Florida since moving there at a young age.

[4] Gooden met Amanda Murphy[P 4] (born (1994-07-24)July 24, 1994[5]) in 2015 after she commented on one of his Vines and they started a long-distance relationship for over a year.

[P 7] After dropping out of community college two times and taking improv classes, Gooden joined Vine, a six-second video platform, in 2013.

[8] Gooden remained known for the Vine several years later, calling it his "catchphrase" and selling merchandise based on it; he was recognized at VidCon as the "Road Work Ahead guy".

[6] Gooden appeared in the Vine-produced web series Camp Unplug (2016), where he first met fellow Viner Danny Gonzalez.

Besides a small Twitter account, he had no other online followings and decided to migrate to YouTube alongside many other Viners.

As he had wanted to transition to longform content, Gooden's initial idea was to create longer comedy sketches that were similar to his Vines.

[2][10][11] Gooden's breakout video was a highly critical review of Jake Paul's live show, uploaded in June 2018.

[P 8] Gonzalez also started a commentary channel on YouTube and the two began traveling to appear in each other's videos, becoming close friends.

The tour, with music, effects, and theatrical elements interspersed with sketches and comedy routines, was their first major live performance and ran from September to October.