Career Timeline of Druski: Major Achievements and Milestones

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 recognized for his sketch comedy, especially "Coulda Been Records." He has collaborated with prominent musicians like Jack Harlow, Drake, and Lil Yachty, appearing in their music videos. Druski has gained significant popularity through his online presence and comedic content.

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Full Timeline Career & Achievements

October 2, 2017: Druski's Instagram Debut

On October 2, 2017, Drew Desbordes began his journey into comedy by posting skits on Instagram under the handle "druski2funny", now known as Druski. He showcased characters like Kyle Rogger, a frat bro, and a ruthless record label executive.

2019: Launch of Coulda Been Records

In 2019, Druski launched Coulda Been Records as an Instagram Live talent-scouting show. The project evolved into a satirical improv record label, inspired by Suge Knight and Sean Combs.

March 9, 2020: Appearance in "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".

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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, further establishing his presence in the music scene.

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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".

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April 2021: Promotional Appearances

In April 2021, Druski appeared in the Squad Up The World | Call of Duty: Warzone Season 3 trailer, and in a Beats By Dre 'It's the Music' TV commercial.

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October 2021: Druski's "Coulda Been Records" and Touring with J. Cole & 21 Savage

In October 2021, Druski satirically offered Meek Mill a contract with Coulda Been Records. Also in October 2021, Druski joined J. Cole and 21 Savage as an opening act for their "The Off-Season Tour".

2022: Touring with Chris Brown and Lil Baby

In the summer of 2022, Druski was an opening act for Chris Brown and Lil Baby on the One of Them Ones tour.

March 2023: Headlining the "Coulda Woulda Shoulda" Comedy Tour

In March 2023, Druski embarked on his first headlining comedy tour, named "Coulda Woulda Shoulda", showcasing a blend of stand-up comedy and live auditions for his Coulda Been Records series.

2023: Launch of 4lifers Entertainment Company

In 2023, Druski launched his 4lifers entertainment company. It encompasses his business ventures, including live touring, TV, film, and web productions, merchandise, licensing, and Coulda Been Records.

2023: Film Debut and Roles

In 2023, Druski made his film debut with a cameo in "House Party" and played a supporting character in "Praise This", directed by Tina Gordon Chism. He was also featured in the final season of Grownish.

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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.

February 2025: Premiere of Coulda Been Love

In February 2025, Druski premiered "Coulda Been Love," a satirical reality dating series on his YouTube channel. The show is a parody of the dating game show format.

March 2025: Conclusion of Coulda Been Love Season 1

In March 2025, the first season of "Coulda Been Love" concluded with over 100 million views, followed by a reunion episode.

2025: Coulda Fest Expanded into a 10-City Tour

In 2025, Druski expanded Coulda Fest into a 10-city arena tour, featuring performances by Snoop Dogg, Wiz Khalifa, A Boogie wit da Hoodie, Lil Yachty, Jack Harlow, Chief Keef, G Herbo, BigXthaPlug, Soulja Boy, Young M.A, Shaboozey, Rod Wave, and more. All dates were reportedly sold out.

2025: Presentation at the ESPY Awards

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

2025: T-Mobile Campaign

In 2025, Druski starred in a campaign for T-Mobile as the company's "Chief Switching Operator," appearing in television commercials alongside Zoe Saldaña and Jeff Bridges.