On October 2, 2017, Desbordes began posting comedic skits and content on his Instagram account under the handle "druski2funny", now Druski. In his early skits, he played a character named Kyle Rogger, a
frat bro, a ruthless record label executive, and others. On March 9, 2020, Desbordes made an appearance in the music video of
Lil Yachty's song "
Oprah's Bank Account". On August 13, 2020, he was featured in the music video of
Drake's song "
Laugh Now Cry Later" featuring
Lil Durk. He would later connect with rapper
Jack Harlow, opening and hosting shows for him. On October 22, 2020, he made a cameo as a school bus driver in the
music video for Jack Harlow's song "
Tyler Herro". He also appears in videos for Jack Harlow's song "Churchill Downs", featuring Drake, and
Chlöe and
Latto's music video for "
For the Night". In 2021, Druski created "Coulda Been Records" as an avenue for artists to join his
Instagram Lives, usually resulting in him teasing them throughout their appearances.
Miami Dolphins 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. Also in October, Desbordes satirically offered
Meek Mill to sign onto Coulda Been Records after Meek Mill said that he did not get paid for his music. Desbordes opened for
Chris Brown and
Lil Baby on the One of Them Ones tour in the summer of 2022. He headlined his first comedy tour, "Coulda Woulda Shoulda", in March 2023. On February 5, 2026, Druski caused controversy at the
15th NFL Honors while announcing the recipient of the 2025
AP NFL Offensive Player of the Year award. While presenting the award alongside
Barry Sanders, Druski mispronounced the last name of the winner,
Jaxon Smith-Njigba of
Seattle Seahawks, saying "The winner decided not to pull up tonight. So, I guess on his behalf, uh, Jaxon Smith-N-nuh-nuh-jigba, Ni-
Nigga-buh. Nigga-buh. Nuh-jee? Nuh-jee-buh, JSN!" In March 2026, Druski released a viral video where he seemingly appeared as
Erika Kirk, the CEO of
Turning Point USA. The video received more than 100 million views within two days of its release, while also causing controversy. ==Business ventures==