Although he began his recording career as a solo artist as one of the last artists on Enjoy Records and one of the first on Vintertainment Records (the same New York-based label owned by Vincent Davis that would later make a name of Hip-Hop artist Joeski Love and bring R&B icon Keith Sweat to ultimate fame), it was when he and a new team of DJs known as the Get Fresh Crew (Barry Bee and Chill Will) along with a newcomer named MC Ricky D (who would later achieve fame as Slick Rick) came to fledgling New Jersey-based Hip-Hop label Danya/Reality Records the following year and recorded “The Show” (which borrowed the melody of the Inspector Gadget theme by Shuki Levy), and “La Di Da Di”, a tune that was completely voiced by MC Ricky D and backed by Doug E’s beat boxing for the entire duration of the song. It was when both of these songs were released on a single (particularly 12″ single) that broke him (and Slick Rick) into stardom. Both “The Show” and “La-Di-Da-Di” are considered two of the all-time greatest early hip hop classics and, as such, make up one of the first and only Hip-Hop singles to have two hit songs on the same record.
“The Show” peaked at #7 in the UK Singles Chart in December 1985.
In 1992, after a four-year hiatus, Doug E. Fresh joined with MC Hammer’s label, Bust It Records and issued one album, Doin’ What I Gotta Do, which (despite some minor acclaim for his single “Bustin’ Out (On Funk)” which sampled the Rick James 1979 single “Bustin’ Out”) was a commercial failure.
In 1993, Doug E. Fresh found a new home at Island Records-affiliated label Gee Street. At the time, he managed only to release one single that contained three songs—”I-ight (Alright),” which was the main song; “Bounce”; and “Freaks”. Although “I-ight” (which originated the now-famous club chant “Heyyyyyy, YO!… I-iiiiight?”) was slated to become the first major hit for Doug in 5 years, it was almost immediately overshadowed by “Freaks”, a Dancehall tune beat-boxed entirely by Doug E. and vocalized mainly by his protégé, a Brooklyn-born Jamaican teenage newcomer named Vicious. The song received major radio and club play, followed by video play when the video was finally produced a few months into 1994. The latter would soon ink a deal with Sony Music’s Epic Records for three years, although he would only release one album, Destination Brooklyn.
In 1995, Slick Rick and Fresh reunited for a track on an album titled Play, which found Fresh back on his feet. The album received positive reviews; Bret Love wrote, “A welcome flashback to the days when guns, drugs, sex, and violence were not the genre’s primary lyrical focus.” Off the Play album also was a track title “Freak It Out” which featured Uncle Luke produced by platinum producer Frankie Cutlass and was also on the Don’t Be a Menace to South Central While Drinking Your Juice in the Hood soundtrack, and was certified a Gold Album by RIAA
2010 saw Fresh make a small comeback in popular culture as rap group Cali Swag District brought back some of his trademark dance moves with their song “Teach Me How to Dougie.” Members of Cali Swag District saw Texas college students doing a local dance created in Dallas called the D-Town Boogie. They recognized it as a modified version of Fresh’s dance moves and decided to create a song that would feature the dance, but also give Fresh his due credit.
On Nov. 8, 2010 Doug E. Fresh appeared at the Soul Train Awards where he taught CNN anchor Wolf Blitzer how to Dougie on stage as part of the show.
On Dec. 10, 2010 Fresh appeared on ESPN First Take to speak about the phenomenon of the Dougie as a sports celebration. As part of the show he, Lomas Brown, and Skip Bayless voted on the best sports related Dougie’s. The Dougie performed by Bayless himself on ESPN First Take was voted by Fresh as the best, although he rated Wolf Blitzer’s Dougie at the Soul Train Awards the best but it had no sports association.
On July 9,2012 Fresh served as a celebrity judge on the Apollo Live TV show.