On October 2, 2017, Desbordes began posting comedic skits and other comedic content on his Instagram account under the handle "druski2funn", now Druski.
[10] In his early skits, he pretended to be a
frat bro named Kyle Rogger, a ruthless record label executive, and other characters, such as Bubba Joe, garnering a wide audience.
Druski crossed paths with then rising artist
Jack Harlow and began opening and hosting shows for him.
[11] On October 22, 2020, Druski made a cameo as a school bus driver in the
music video for Jack Harlow's song "
Tyler Herro."
[12] On March 9, 2020, he was featured on
Lil Yachty's song "
Oprah's Bank Account."
[13] On August 13, 2020, Desbordes was featured in the music video of
Drake's song "
Laugh Now Cry Later" featuring
Lil Durk.
[14][15] Drew also appears in videos for Jack Harlow's song "Churchill Downs", featuring Drake, and
Chlöe and
Latto's music video for
For the Night.
[16]
In 2021,
Diddy (through his
Revolt) and
Adidas announced a new series called
Sneakin’ In With Druski, with Desbordes as the host.
[17] The series has featured people like
Snoop Dogg,
Teyana Taylor, and Yung Miami (from
City Girls) since its launch.
[18] That same year, Desbordes created the satirical label Coulda Been Records as a way for artists to come onto his
Instagram Lives, usually resulting in him teasing them throughout their time on.
[19] Baltimore Ravens wide receiver
Odell Beckham Jr. struck up a friendship with Druski upon finding his videos, and invited the comedian to stay at his home during the
COVID-19 pandemic.
[8] Druski was an opening act for
J. Cole and
21 Savage's
The Off-Season Tour throughout September and October 2021.
[20] Also in October, Desbordes satirically offered
Meek Mill to sign onto Coulda Been Records after Meek Mill said that he didn't get paid for his music.
[21][22][23]
Desbordes launched his 4lifers entertainment company in 2023, which serves as the umbrella company for his business ventures. Those range from live touring, TV/Film/Web productions, merchandise, licensing, and Coulda Been Records.
[24]