In early 2015, Hamilton signed with Republic Records to release the single "New York Raining" (featuring Rita Ora), which was used for the television series Empire.
[6] Along with his solo career, he was part of the group The Chosen Few, as well as Lupe Fiasco's alternative hip hop collective All City Chess Club.
His music and public image contained frequent tributes to the video game series Sonic the Hedgehog.
He was exposed to music at an early age: "My mother was an entertainment journalist for the Cleveland Call and Post, so she would take me with her to events when I was just a baby."
Hamilton would leave from his mother's home at the age of 18 and would at times be homeless spending his nights at his friends' houses.
Hamilton stated, "The Lab (FDA's studio) means so much to me, because when I literally didn't have anywhere else to go in the world, I can just go into my beloved alma mater and purge myself creatively."
Hamilton would later meet his future manager Le'Roy Benros after offering to help with a music event that he was organizing.
[8] When Benros eventually heard his music he was "blown away" and arranged a meeting at Hamilton's high school in Harlem.
[8] Benros set about promoting his first client in any way that he could, burning CDs, putting him on at showcases and securing his first appearance on the influential blog "You Heard That New".
[31][32][33] In 2008, Hamilton was chosen for the XXL's 2009 Freshmen cover issue alongside fellow rappers Wale, B.o.B, Asher Roth, Cory Gunz, Blu, Mickey Factz, Ace Hood, Curren$y and Kid Cudi.
The mixtape lyrically followed the story of a fan who had a romantic obsession with the singer-songwriter Rihanna, and instrumentally included various samples of her music.
According to Hamilton's blog at the time, the album was to be released digitally on June 23, 2009,[39] and the physical copy in stores on August 25, 2009.
There was also a physical copy of the album that would have to be purchased in stores that included a DVD of animated videos to help the listener get a better feel for the music.
[42] A handful of Dilla's closest associates through hip hop began speaking out against Hamilton's use of the name and its connection to his music.
[43] After months of speculation, the album was never released as a result of Hamilton getting dropped from Interscope on September 19, 2009, for multiple reasons, including but not limited to his poor performance at a Penn State rap battle and his unapproved crediting of J Dilla.
[44] Manager Le'Roy Benros later explained why he felt Hamilton's career stalled by telling HitQuarters: "I think things happened too fast.
[49] Also in March, Hamilton dedicated a song called "Choices (A Wave to Alex)" in honor of a friend who died after getting in the car with a drunk driver.
[51] On July 3, 2010, Hamilton released six mixtapes entitled Well This Isn't Awkward (Winner Takes All), Autumn Harvest, Gynophobia, Atlantis and A..., 10 Things I Hate About Me and The L Word II (INcomplete).
[55] On September 23, 2011, one day after his discharge from Community Assessment and Treatment Services Rehab, Hamilton released two mixtapes, Gynophobia 2 and C.A.T.S.
[59] The next year, Hamilton announced through Twitter hat he was releasing an independent album entitled Ill Doesn't Mean Classic.
[60][61][62] On July 30, 2012, Hamilton released a collaboration mixtape entitled Cinematic Hallucinations: The Bully And The Pet with rapper S.K.E.
My Heart was originally supposed to be released as Hamilton's debut studio album in 2010 while he was signed to NewCo Records but it was later shelved.
Unharmed, he wandered to Quicken Loans Arena where he began playing what he says was an imaginary basketball with exiting Cavalier fans.
[79] A week later, Hamilton performed a collaboration track with singer-songwriter Rita Ora, entitled "New York Raining".
[95] On September 17, 2015, Hamilton would reveal via Twitter that he had push the release date back for his upcoming EP The Black Box.
[104] On June 15, 2019, Charles Hamilton released "Ralph Nader", his first live-action music video since "New York Raining".
[107] Controversial, containing no samples, is an original composition from front to back, with Serious Truth having played the synth, bass, electric piano and drum machine throughout the entire project.
[108][109] Writing and recording credits are split between Charles Hamilton and Serious Truth, with the latter also handling the cover artwork as well as audio engineering and post production aspects.
[114][115] Hamilton has also named artists Incubus, N.E.R.D., Jay Z, Modest Mouse, Korn, Dr. Dre, Thelonious Monk, Aerosmith, 50 Cent, Marilyn Manson, The Alchemist, The Isley Brothers, Kanye West, Nine Inch Nails, Hi-Tek, DMX and Mase as other influences in his music, stating "I just love good music.
"[11][33][116] Hamilton has been known for his clear enunciation and his story-telling rhymes focusing on depression, hope, social injustice, drugs, Sega, women and religion.