In 1997, Anthony Tiffith began managing producers who produced for rappers such as The Game and Juvenile, among others. In 2003, Tiffith found a then-16 year old Kendrick Lamar, a Compton native, who at the time went by K-Dot and had just released his first mixtape, which gained recognition and earned the young rapper a buzz in his local area. Tiffith saw so much potential in Lamar, he signed him off the strength of his first mixtape. It wasn't until 2005 that TDE started to gain success with another California-based rapper, Watts' own Jay Rock. Following Rock's signing, TDE signed joint venture deals with Warner Bros. and later Asylum Records. However, following the merger, TDE began planning an exit strategy after the labels failed to handle Rock's debut Follow Me Home properly.
In 2007, Carson-based rapper Ab-Soul, was added to the Top Dawg roster. On May 10, 2008 the label released a compilation mixtape titled Do It Nigga Squad, Volume 1, which features songs by members of the label's roster, with other appearances coming from fellow American rappers Schoolboy Q, Lil Wayne and will.i.am. All songs on the mixtape were mixed by Top Dawg's resident engineer Derek "MixedByAli" Ali, much like a majority of their releases are. In October 2008, Jay Rock released his commercial debut single "All My Life (In the Ghetto)," which was included as the last track on the aforementioned mixtape and features Lil Wayne and will.i.am. In 2009, Los Angeles-based rapper Schoolboy Q signed with TDE after being affiliated with the label since 2006. In 2009, once they were all signed to the label, Schoolboy Q suggested that he, Lamar, Rock and Ab-Soul form a rap group. They all agreed and all four artists formed the hip hop group Black Hippy.
In 2010, TDE issued Kendrick Lamar's fourth mixtape Overly Dedicated exclusively to digital retailers, such as iTunes. Four more projects followed route, Jay Rock's mixtape Black Friday (2010), Schoolboy Q's Setbacks (2011), Ab-Soul's Longterm Mentality (2011) and Kendrick Lamar's Section.80 (2011); the latter of which was critically acclaimed and peaked at number 113 on the Billboard 200. The first studio album released to stores and online retailers was Jay Rock's Follow Me Home album, released on July 26, 2011, with Tech N9ne's Strange Music. The album debuted at number 83 on the Billboard 200, selling 5,300 copies in its first week.
In March 2012, MTV reported that Top Dawg Entertainment closed a joint venturedeal with Interscope Records and Aftermath Entertainment. Under the new deal, Kendrick Lamar's debut studio album, good kid, m.A.A.d city would be jointly released via Top Dawg, Interscope and Aftermath, while releases from the rest of Black Hippy would be released by Top Dawg and Interscope. In August 2012, Top Dawg Entertainment wanted to show appreciation to their fans. Doing what they called "TDEFamAppreciationWeek", they released solo tracks from each of the Black Hippy members and a video of Lamar and Q acting out on the tour bus. Kendrick Lamar was the first to release his major label debut, with good kid, m.A.A.d city hitting stores on October 22, 2012. The album was highly acclaimed and went on to become certified Platinum by the Recording Industry Association of America (RIAA). Schoolboy Q subsequently began recording his major label debut Oxymoron, which was released February 25, 2014.
In June 2013, Top Dawg announced they were planning to sign two more artists, with the first being reported as Tennessee native, Isaiah Rashad. On July 14, it was revealed Top Dawg had signed an up-and-coming female singer named SZA, to the label. In August 2013, during an interview with Vibe, CEO Anthony Tiffith spoke on comparisons to Death Row Records, another label based in Southern California, run by Comptonite Marion “Suge” Knight, that had released albums from Dr. Dre, Snoop Dogg, Tupac Shakur and others during the 1990s. Tiffith also said that he learned several lessons from his first major label contract; a deal with Warner Bros. Records for Jay Rock, that lasted from 2006 until 2010. Tennessee-based rapper Isaiah Rashad's signing to Top Dawg Entertainment was officially announced on September 20, 2013.
In October 2013, at the BET Hip Hop Awards, Kendrick Lamar won five awards, including Album of the Year and Lyricist of the Year, the latter of which he also won the year before. At the award ceremony, Schoolboy Q performed his debut album's lead single "Collard Greens", with Lamar following him, performing "Money Trees", alongside Jay Rock. Lamar, Rock and Schoolboy Q were also featured in a cypher, along with Ab-Soul and newcomer Isaiah Rashad, which was presented by BET, in an annual effort to showcase a specific label's roster, with GOOD Music in 2010, Shady Records and MMG in 2011, as well as Grand Hustle and Ruff Ryders in 2012, respectively. In an October 2013 interview with XXL, co-president Terrence "Punch" Henderson confirmed that the original reports of the record label being distributed by Interscope Records were incorrect. He said only Schoolboy Q and Kendrick Lamar ever had solo record deals with Interscope Records, while the label was currently looking for a distribution deal for the entire label.
In November 2013, Kendrick Lamar was named GQ's "Rapper of the Year," and was featured on the cover of the magazine's "Men of the Year" issue. Following the issue's release, TDE's CEO Anthony "Top Dawg" Tiffith, pulled Kendrick Lamar from performing at GQ 's party that accompanies the issue, calling out writer Steve Marsh's profile, "Kendrick Lamar: Rapper of the Year," for its "racial overtones," such as comparisons to Suge Knight and Death Row Records.GQ editor-in-chief Jim Nelson, responded saying: "Kendrick Lamar is one of the most talented new musicians to arrive on the scene in years," the EIC said in a statement that was posted to the magazine's website. "That's the reason we chose to celebrate him, wrote an incredibly positive article declaring him the next King of Rap, and gave him our highest honor: putting him on the cover of our Men of the Year issue. I'm not sure how you can spin that into a bad thing, and I encourage anyone interested to read the story and see for themselves."
After not releasing an album the entire year, on December 21, 2013, CEO Anthony "Top Dawg" Tiffith revealed that he plans on the entire label's roster releasing solo albums in 2014, starting with Schoolboy Q's Oxymoron on February 25, 2014. However, it was later confirmed that Isaiah Rashad would make his debut with Cilvia Demo on January 28, 2014.
On March 26, 2014, R&B artist SZA released the single "Child's Play" featuring Chance The Rapper and produced by XXYYXX. The song is taken off of her upcoming EP "Z" due for release on April 8.
Top Dawg Entertainment houses a production team named Digi+Phonics, composed of music producers Dave Free, Willie B, Tae Beast and Sounwave. They have formed the majority of the production on the many of the TDE releases. King Blue, also known as Blue The Misfit, was once half of the musical duo Sore Losers and is also signed to Top Dawg as a producer, producing songs such as Kendrick Lamar's "P&P", Schoolboy Q's "To tha Beat (F’d Up)", Mac Miller’s "Down the Rabbit Hole" and most recently, Ab-Soul’s "Mixed Emotions". As is production team THC, a trio of producers who have produced several songs by members of Black Hippy, including Kendrick Lamar's "Cartoon & Cereal" and "m.A.A.d City", as well as Schoolboy Q's "Collard Greens", among several other tracks.