Your Old Droog

Droog's family emigrated to the United States from Ukraine when he was four years old.[3] As a young rap enthusiast growing up in Brooklyn, Droog first developed his craft in lunchroom battles in school.[3]

In April 2014, he released the song "Nutty Bars", which generated a significant amount of buzz due to comparisons to Nas and the otherwise lack of information about the artist.[5] The speculation began after Sacha Jenkins, a longtime associate of Nas, made a short positive review of the rapper on Mass Appeal with the sub-heading "Who is this guy? None of your damn business! Just enjoy the music and stop asking questions."[5][6] The 10-song Your Old Droog EP was released soon after in June on SoundCloud, produced by Droog and RTNC (later known as Mono En Stereo [7]). In August, Droog revealed himself in an interview with The New Yorker and soon showed his face for the first time in a video of him freestyling.[8] At the time, he embraced the publicity and speculation regarding his identity, expressing that "This is like my street team, why would I stop free publicity?"[2] He played his first concert on September 3 to a sold-out crowd at Webster Hall.[1] His debut self-titled album was released digitally on November 26, which included the 10 songs from the EP along with 8 new songs produced by EL RTNC.[4] A limited edition of the album was released on vinyl shortly before the digital release.[9]

Kinison EP, Your Old Droog's second EP, was released on February 4, 2015, again on SoundCloud.[10] Kinison's lyrical theme is that of Droog's appreciation of rock music as a child, with songs named after Rage Against the Machine, Porno for Pyros, and Sonic Youth.[11] That February and March, Your Old Droog supported DJ Premier and Royce da 5'9" on their PRhyme Tour.[10] Your Old Droog's third EP, The Nicest, was released on July 17, 2015.

In February 2017, Your Old Droog released What Happened to Fire?, an EP in collaboration with Ratking rapper Wiki. Later that month, Packs, Droog's second full-length album, was announced to be released on March 10, 2017. To coincide with the announcement, a music video for the album's single "Help" was released, featuring Wiki and Edan.[12]

Droog release three full-length albums in 2019, with It Wasn't Even Close, Transportation, and Jewelry. It Wasn't Even Close was produced by Mach-Hommy[7] and came out on April 20, 2019, featuring appearances by DOOM, and Wiki.[13] Transportation was produced again by Mono En Stereo[7] and was released in June.[14] Jewelry was released on December 23, 2019, featuring collaborations with the album's executive producer Mach-Hommy as well as DOOM, Matisyahu, Quelle Chris, Edan, and Cohen Beats.[15][14] The album is a celebration of his Jewish heritage, labeled a "A Chanukah Celebration" with Your Old Droog stating "I'm no longer going to diminish my heritage for your comfort, some people hate simply for the sake of hating, let them crumble under the weight of that burden...we will celebrate light and life...I'm a Jew in America. This is my story. Shalom."[16]

Your Old Droog has been extensively compared to fellow New York rapper Nas, to the point of theories being developed that his debut EP was actually recorded by Nas under an alter ego.[1] Droog has appreciated the comparison and deemed it a compliment; he also named Big Daddy Kane,[1] Big L, and Kool G Rap as influences,[2] as well as Beanie Sigel, Freeway, Cassidy, and Lloyd Banks.[3] He has named MF DOOM as one of his favorites, from whom he has learned his approach to privacy as a rapper in the public eye.[5]