2005–2009: Early career and debut album
Plan B first appeared with the track "Cap Back", produced by DJ Wonder (formerly of Roll Deep), on the grime compilation album Run the Road (2005). His first single "Kidz"/"Dead and Buried" was also released in 2005 as a limited edition 7" vinyl on his own label Pet Cemetery Records. He soon gained a recording contract with 679 Recordings and released his second double A-side single "Sick 2 Def"/"No Good", filming his debut music video for "No Good".
In early 2006, Plan B released a video-only download single for "Missing Links", which later had to be re-recorded because he did not gain sample permission from Radiohead for the use of "Pyramid Song". He also released his first mixtape It's Time 4 Plan B with the May 2006 issue of Hip Hop Connection magazine. On 23 June 2006, Plan B made his first television appearance on Later... with Jools Holland, performing an acoustic version of "Mama (Loves a Crackhead)". His début album Who Needs Actions When You Got Words was recorded with producers Paul Epworth, Fraser T Smith and the Earlies, and was released 26 June 2006, charting the following week at number thirty on the UK Albums Chart. The album gained positive reviews from most critics, including a five-star review from The Guardian's Alexis Petridis. In July 2006, "Mama (Loves a Crackhead)" was released as a single, becoming the first Plan B song to appear on the UK Singles Chart, peaking at number forty one. In 2006, Paul Epworth and Plan B collaborated again on the track "More Is Enough" by Epic Man (Paul Epworth).
After touring throughout 2006, playing at festivals such as Reading and Leeds, a music video was filmed for "No More Eatin'" to accompany the release of Plan B's Live at The Pet Cemetery EP on 30 October 2006 (including a new version of "No More Eatin'" and two b-sides). On 11 December 2006, he released the Remixes EP (which included the Hadouken! remix of "No More Eatin'"). During his January–February 2007 tour (which included support from Professor Green, Example, Killa Kela and Hadouken!), Plan B released his second mixtape Paint It Blacker, containing bootleg recordings of songs by artists such as the Rolling Stones, Nirvana, Radiohead, Coldplay, Leonard Cohen and José González with producers Sem, Beni G from the Mixologists and Amir Amor. In 2007, Plan B re-released the song "No Good" with new remixes, and a music video was filmed for the b-side "Bizness Woman" (featuring beatboxer Kila Kella). Also in 2007, Plan B featured on songs by other artists such as Professor Green, Killa Kela, Skrein, Shameless and the Mitchell Brothers.
With a supporting role in the film Adulthood (2008), Plan B recorded three songs for the film's soundtrack – "End in the Streets", "On It 08" with Adam Deacon and "I Need Love" featuring Raleigh Ritchie. Plan B also featured on the Chase & Status single "Pieces", which topped the UK Dance Chart in 2008 and peaked at number seventy on the UK Singles Chart. In 2009, Plan B recorded "Shifty" with Riz MC and Sway, which was lifted from the soundtrack to Eran Creevy's film Shifty (2009), starring Riz Ahmed (Riz MC) and Daniel Mays. Also in 2009, Plan B played Noel Winters in Harry Brown, and achieved his first Top ten hit single with "End Credits", another collaboration with Chase & Status which featured in the soundtrack for Harry Brown.