His first single “Pressure”, featuring Ginuwine peaked at number 10 on the Canadian CHR radio charts, and number one on MuchMusic’s Video chart. In April 2007, Belly released the video for his second single “Don’t Be Shy”, featuring Nina Sky, as well as the video for “History of Violence” directed by Martin Verigin and Jeffrey Hagerman. The video remains his most controversial record to date. In “History of Violence”, Belly explains his views on the Israeli–Palestinian conflict and the War in Iraq.

During the 2007 NHL Playoffs, as the Ottawa Senators were competing, Belly released a single entitled “Bandwagon” (produced by Hussain). When the Senators made the Stanley Cup Finals, Belly released a second version of the song which featured goaltender Ray Emery.

His debut album, The Revolution, was released on 5 June 2007. This double disc album was divided into two sections: The People and The System. The People contained more in depth songs, such as “History of Violence”, “Follow Me”, and “Revolutionary”, where he challenges his listeners to discover the facts regarding the Middle-East situation. Other songs on this disc include “People Change”, “Leave Me Alone” where he talks about his longtime friends and the memories that he kept from them. The System contained his hit singles “Ridin'”, and “Pleasure”.

The Revolution achieved Gold sales in Canada and won the 2008 Juno Award for Rap Recording of the Year. Singles from The Revolution won two MuchMusic Video Awards for Best Rap Video; “Pressure” in 2007 and “Ridin'” in 2008.

His mixtape, Sleepless Nights 1.5 was released April 2012. The first single “Hot Girl”, featuring Snoop Dogg was released on 8 September 2009.

Second single “To The Top”, featuring Ava, was released in 2010. Belly’s first single of 2011 was “Back Against the Wall”, featuring Grammy Award-nominated singer Kobe Honeycutt.

Belly also released a body of work that was a compilation of songs he had worked on with Dogg Pound rapper Kurupt some time after his first album The Revolution. Some songs were unreleased with a few that had seen release dates on previous mixtapes. This mixtape was called Belly & Kurupt The Lost Tapes 2008 hosted yet again by DJ Ill Will. In 2011, Belly released another new mixtape titled The Greatest Dream I Never Had which he has said will have no features.

In May 2015, Belly released his newest mixtape, entitled Up for Days. It featured 10 tracks, including four collaborations with Travis Scott, Juelz Santana, French Montana, XO-label head, and The Weeknd in addition to six solo tracks. On 24 November 2015, it was announced that he had signed with Jay-Z’s Roc Nation label.

Belly was also prominently featured on The Weeknd’s album, Beauty Behind the Madness in August 2015, earning six writing credits on songs like Often, The Hills, Shameless, Earned It, In the Night and As You Are.

In February 2016, he released the lead single to his upcoming project “Zanzibar”, featuring American rapper Juicy J. On 27 May 2016, he released Another Day in Paradise, which featured guest appearances from Travis Scott, Lil Wayne, Kehlani, Starrah, Waka Flocka, Juicy J and B-Real.

On 11 November 2016, he released his tenth mixtape, Inzombia which had 11 tracks. It featured guest appearances from Young Thug, Zack, Nav, Future, Ty Dolla $ign, Jadakiss and Ashanti. The mixtape was supported by two singles; “Consuela” and “The Day I Met You”. Later that month, The Weeknd released his third studio album, Starboy, with Belly having writing credits on 9 of the 18 songs, such as Party Monster, False Alarm, Rockin’, Six Feet Under, “Love to Lay”, “A Lonely Night”, “Ordinary Life”, “Nothing Without You” and All I Know.

On 6 October 2017, Belly released Mumble Rap which the mixtape being executive produced by fellow Canadian producer Boi-1da.

Belly released “4 Days”, on 22 March 2018, in promoting his upcoming second album. The song features American rapper YG, and production from Mustard. The music video was released 26 March 2018.

Belly served as a co-writer on The Weeknd’s EP, My Dear Melancholy, on 30 March 2018, on the song “Try Me”.

Belly released the lead single to his second upcoming studio album Immigrant on 5 April 2018, titled “Maintain”, which featured Nav. The music video was released 11 May 2018. The second single “What You Want” was released 24 May 2018. The music video was released 30 May 2018. It features guest vocals from Canadian musician, The Weeknd. Immigrant was officially released 12 October 2018. The album also features guest appearances from Zack, French Montana, Meek Mill, Yo Gotti and M.I.A..

On 30 July 2019, Belly filed a lawsuit against Coachella Music LLC, Goldenvoice LLC, and IPS Security Incorporated alleging assault and battery, negligence, and emotional distress in response to an incident which occurred during the 2018 Coachella Music Festival. A video obtained by TMZ shows festival security staff pushing Belly up against a security barrier and repeatedly punching him.