Career Timeline of Druski: Major Achievements and Milestones

By Popular Timelines Editorial Team · Updated: May 2, 2026

From career breakthroughs to professional milestones, explore how Druski made an impact.

Drew Desbordes, known as Druski, is an American comedian, actor, and social media influencer. He's gained recognition for his sketch comedy, particularly his 'Coulda Been Records' skits. Druski is also known for his appearances in music videos of prominent artists like Drake, Jack Harlow, and Lil Yachty, expanding his reach and solidifying his presence in the entertainment industry.

Sections (2)

Full Timeline Career & Achievements

October 2, 2017: Druski's Instagram Debut

On October 2, 2017, Drew Desbordes, under the handle "druski2funny", now Druski, began posting comedic skits and content on his Instagram account. Early skits featured characters like Kyle Rogger, a frat bro, and a record label executive.

March 9, 2020: Appearance in Lil Yachty's "Oprah's Bank Account" music video

On March 9, 2020, Druski appeared in the music video for Lil Yachty's song "Oprah's Bank Account".

Loading Video...

August 13, 2020: Feature in Drake's "Laugh Now Cry Later" music video

On August 13, 2020, Druski was featured in the music video for Drake's song "Laugh Now Cry Later" featuring Lil Durk.

Loading Video...

October 22, 2020: Cameo in Jack Harlow's "Tyler Herro" music video

On October 22, 2020, Druski made a cameo appearance as a school bus driver in the music video for Jack Harlow's song "Tyler Herro".

Loading Video...

October 2021: The Off-Season Tour and Coulda Been Records Offer to Meek Mill

In October 2021, Druski was an opening act for J. Cole and 21 Savage's The Off-Season Tour. Also in October, he satirically offered Meek Mill to sign onto Coulda Been Records after Meek Mill said that he did not get paid for his music.

March 2023: Coulda Woulda Shoulda Comedy Tour

In March 2023, Druski headlined his first comedy tour, "Coulda Woulda Shoulda", featuring stand-up comedy and live auditions for Coulda Been Records.

2024: Launch of Coulda Fest

In the fall of 2024, Druski launched Coulda Fest with a sold-out show at the State Farm Arena in Atlanta, featuring musical performances.

2025: ESPY Awards Presentation

In 2025, Druski presented the award for Best Team at the ESPY Awards.

2025: Forbes Top Creators List and Coulda Fest tour dates

In 2025, Forbes magazine ranked Druski #9 on its top creators list. His Coulda Fest was expanded into a 10-city arena tour with all dates reportedly sold out.

February 5, 2026: NFL Honors Controversy

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. He mispronounced the last name of the winner, Jaxon Smith-Njigba.

March 2026: Viral Video as Erika Kirk

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 but also caused controversy.